Strategies for introducing sulfur atom in a sugar ring: synthesis of 5-thioaldopyranoses and their NMR data

References

• Adley TJ, Owen LN. Thiosugars with sulfur in the ring. Proc Chem Soc Lond. 1961: 418.
   Google Scholar
• Schwarz J, Yule K. d-xylothiapyranose-A sugar with sulphur in the ring. Proc Chem Soc Lond. 1961: 417.
   Google Scholar
• Whistler RL, Feather MS, Ingles DL. Introduction of a new hetero atom into a sugar ring. J Am Chem Soc. 1962;84:122–122.
   Google Scholar
• McNaught AD. Nomenclature of carbohydrates. Carbohydr Res. 1997;297:1–92.
   Google Scholar
• N.A. Nomenclature of Carbohydrates, (Recommendations 1996). 2-Carb-15. Thio sugars and other chalcogen analogues and 2-Carb-34. Replacement of ring oxygen by other elements. Adv Carbohydr Chem Biochem. 1997;52:44–177.
   Google Scholar
• Greimel P, Spreitz J, Sprenger FKF, et al. Sugars with endocyclic heteroatoms other than oxygen. The Organic Chemistry of Sugars. Boca Raton: CRC Press; 2005; p. 383–424.
   Google Scholar
• Inmaculada R, Pierre V, Zbigniew JW. Synthesis and biological properties of monothiosaccharides. Curr Org Chem. 2001;5:1177–1214.
   Google Scholar
• Yuasa H, Izumi M, Hashimoto H. Thiasugars: potential glycosidase inhibitors. Curr Top Med Chem. 2009;9:76–86.
   Google Scholar
• Horton D, Wander JD. The carbohydrate. chemistry and biochemistry. In: Pigman W, Horton D, editor. Vol. IB. 2nd ed. New York: Academic Press; 1980. p. 799–842.
   Google Scholar
• Hashimoto H, Fujimori T, Yuasa H. Synthesis of 5-thio-l-fucose and its inhibitory effect on fucosidase. J Carbohydrate Chemistry. 1990;9:683–694.
   Google Scholar
• Kajimoto T, Liu KKC, Pederson RL, et al. Enzyme-catalyzed aldol condensation for asymmetric synthesis of azasugars: synthesis, evaluation, and modeling of glycosidase inhibitors. J Am Chem Soc. 1991;113:6187–6196.
   Google Scholar
• (a) Witczak ZJ. Thio sugars: biological relevance as potential new therapeutics. Curr Med Chem. 1999;6:165–178. (b) Dey PM, Witczak ZJ. Functionalized S-thio-di- and S-oligosaccharide precursors as templates for novel SLex/a mimetic antimetastatic agents. Mini Rev Med Chem. 2003;3:271–80.
   Google Scholar
• Horton D, Hutson DH. Developments in the chemistry of thiosugars. In: Wolfrom ML, Tipson RS, editor. Advances in carbohydrate chemistry. Vol. 18. California: Academic Press; 1963. p. 123–199.
   Google Scholar
• Paulsen H, Todt K. Cyclic monosaccharides having nitrogen or sulfur in the ring (Translated from the German) by M.L. Wolfrom. In: Wolfrom ML, Tipson RS, editor. Advances in carbohydrate chemistry. Vol. 23. Amsterdam: Academic Press; 1968. p. 115–232.
   Google Scholar
• Whistler RL, Anisuzzaman AKM. Methods for introducing atoms other than oxygen into sugar rings. Synthetic methods for carbohydrates. ACS Symp Ser: Am Chem Soc. 1977;39:133–154.
   Google Scholar
• Nicotra F. Modified carbohydrates and carbohydrate analogues. In: Boons G-J, editor. Carbohydrate chemistry. London: Blackie Academic and Professional; 1998. p. 384–429.
   Google Scholar
• Hale KJ, Richardson AC. Chemical synthesis of monosaccharides. In: Finch P, editor. Carbohydrates: structures, syntheses and dynamics. Dordrecht: Springer Netherlands; 1999. p. 47–106.
   Google Scholar
• Mehta S, Pinto BM. Phenyl selenoglycosides as a versatile glycosylating agents in oligosaccharides synthesis and the chemical synthesis of disaccharides containing sulfur and selenium. In: Khan SH, O’Neill RA, editor. Modern methods in carbohydrate synthesis. Amsterdam: Harwood Academic Publishers; 1996. p. 107–129.
   Google Scholar
• Yuasa H, Hashimoto H. Replacing the ring oxygen of carbohydrates with sulfur: its biological and chemical consequences. Rev Heteroatom Chem. 1999;19:35–65.
   Google Scholar
• Fernandez-Bolanos JG, Al-Masoudi NA, Maya I. Sugar derivatives having sulfur in the ring. Adv Carbohydr Chem Biochem. 2001;57:21–98.
   Google Scholar
• Inmaculada R, Pierre V. The synthesis of disaccharides, oligosaccharides and analogues containing thiosugars. Curr Org Chem. 2002;6:471–491.
   Google Scholar
• Witczak ZJ, Culhane JM. Thiosugars: new perspectives regarding availability and potential biochemical and medicinal applications. Appl Microbiol Biotechnol. 2005;69:237–244.
   Google Scholar
• Malone A, Scanlan EM. Applications of thiyl radical cyclizations for the synthesis of thiosugars. Org Lett. 2013;15:504–507.
   Google Scholar
• Malone A, Scanlan EM. Applications of 5-exo-trig thiyl radical cyclizations for the synthesis of thiosugars. J Org Chem. 2013;78:10917–10930.
   Google Scholar
• Capon RJ, MacLeod JK. 5-Thio-d-mannose from the marine sponge Clathria pyramida (Lendenfeld). The first example of a naturally occurring 5-thiosugar. J Chem Soc Chem Commun. 1987;15:1200–1201.
   Google Scholar
• Yoshikawa M, Murakami T, Shimada H, et al. Salacinol, potent antidiabetic principle with unique thiosugar sulfonium sulfate structure from the Ayurvedic traditional medicine Salacia reticulata in Sri Lanka and India. Tetrahedron Lett. 1997;38:8367–8370.
   Google Scholar
• Yoshikawa M, Murakami T, Yashiro K, et al. Kotalanol, a potent α-glucosidase inhibitor with thiosugar sulfonium sulfate structure, from antidiabetic Ayurvedic medicine Salacia reticulata. Chem Pharm Bull. 1998;46:1339–1340.
   Google Scholar
• Oishi H, Noto T, Sasaki H, et al. Thiolactomycin, a new antibiotic. J Antibiot. 1982;35:391–395.
   Google Scholar
• Sasaki H, Oishi H, Hayashi T, et al. Thiolactomycin, a new antibiotic. J Antibiot. 1982;35:396–400.
   Google Scholar
• Wong CH, Ichikawa Y, Krach T, et al. Probing the acceptor specificity of.beta.-1,4-galactosyltransferase for the development of enzymatic synthesis of novel oligosaccharides. J Am Chem Soc. 1991;113:8137–8145.
   Google Scholar
• Mehta S, Andrews JS, Svensson B, et al. Synthesis and enzymic activity of novel glycosidase inhibitors containing sulfur and selenium. J Am Chem Soc. 1995;117:9783–9790.
   Google Scholar
• Andrews JS, Weimar T, Frandsen TP, et al. Novel disaccharides containing sulfur in the ring and nitrogen in the interglycosidic linkage. conformation of methyl 5’-thio-4-N-.alpha.-maltoside bound to glucoamylase and its activity as a competitive inhibitor. J Am Chem Soc. 1995;117:10799–10804.
   Google Scholar
• Tsuruta O, Yuasa H, Hashimoto H, et al. Synthesis of GDP-5-thiosugars and their use as glycosyl donor substrates for glycosyltransferases. J Org Chem. 2003;68:6400–6406.
   Google Scholar
• Matsuda H, Ohara K, Morii Y, et al. α-Selective glycosylation with 5-thioglucopyranosyl donors; synthesis of an IsoMaltotetraoside mimic composed of 5-thioglucopyranose units. Bioorg Med Chem Lett. 2003;13:1063–1066.
   Google Scholar
• Stachel H-D, Schachtner J, Lotter H. Synthesis of (±) – thioascorbic acid. Tetrahedron. 1993;49:4871–4880.
   Google Scholar
• Bellamy F, Barberousse V, Martin N, et al. Thioxyloside derivatives as orally active venous antithrombotics. Eur J Med Chem. 1995;30:101s–115s.
   Google Scholar
• Bozó É, Boros S, Kuszmann J. Synthesis of 4-cyanophenyl 2-azido-2-deoxy-and 3-azido-3-deoxy-1, 5-dithio-β-d-xylopyranosides. Carbohydr Res. 1997;301:23–32.
   Google Scholar
• Bozó É, Boros S, Kuszmann J. Synthesis of 4-cyanophenyl 4-azido-4-deoxy-1, 5-dithio-β-d-xylopyranoside. Carbohydr Res. 1997;302:149–162.
   Google Scholar
• Samreth S, Barberousse V, Bellamy F, et al. Thioxyloside derivatives, a novel oral venous antithrombotic. Actual Chim Ther. 1994;21:23–33.
   Google Scholar
• Bellamy F, Horton D, Millet J, et al. Glycosylated derivatives of benzophenone, benzhydrol and benzhydril as potential venous antithrombotic agents. J Med Chem. 1993;36:898–903.
   Google Scholar
• Schuetz RD, Jacobs RL. The preparation and desulfurization of some unsymmetrically substituted thiiranes. J Org Chem. 1961;26:3467–3471.
   Google Scholar
• Gao Y, Sharpless K. Titanium isopropoxide mediated formation of 2, 3-epithio alcohols from 2, 3-epoxy alcohols. J Org Chem. 1988;53:4114–4116.
   Google Scholar
• Uenishi J, Motoyamaand M, Takahashi K. Asymmetric synthesis of d- and l-2-deoxy-4-thioriboscs. Tetrahedron: Asymmetry. 1994;5:101–110.
   Google Scholar
• Izraelewicz MH, Nur M, Spring RT, et al. Studies on the reaction of thiiranes with tributyltin hydride. J Org Chem. 1995;60:470–472.
   Google Scholar
• Kamata M, Murayama K, Miyashi T. Aminium radical salt catalyzed desulphurization of thiiranes: an efficient preparation of arylsubstituted olefins. Tetrahedron Lett. 1989;30:4129–4132.
   Google Scholar
• Witczak ZJ, Poplawski T, Czubatka A, et al. A potential CARB-pharmacophore for antineoplastic activity: part 1. Bioorg Med Chem Lett. 2014;24:1752–1757.
   Google Scholar
• Whistler RL, Lake WC. Inhibition of cellular transport processes by 5-thio-d-glucopyranose. Biochem J. 1972;130:919–925.
   Google Scholar
• Nakamura M, Hall PF. Effect of 5-thio-d-glucose on protein synthesis in vitro by various types of cells from rat testes. J Reprod Fertil. 1977;49:395–397.
   Google Scholar
• Bushway AA, Keenan TW. 5-Thio-d-glucose is an acceptor for UDP-galactose: d-glucose 1-galactosyltransferase. Biochem Biophys Res Commun. 1978;81:305–309.
   Google Scholar
• Kim SH, Kim JH, Hahn EW. Selective potentiation of hyperthermic killing of hypoxic cells by 5-thio-d-glucose. Cancer Res. 1978;38:2935–2938.
   Google Scholar
• Nayak UG, Whistler RL. Synthesis of 5-thio-d-glucose. J Org Chem. 1969;34:97–100.
   Google Scholar
• Whistler RL, Lake WC. [50] – 5-thio-α-d-glucopyranose: via conversion of a terminal oxirane ring to a terminal thiirane ring. In: Whistler RL, BeMiller JN, editor. General carbohydrate method. Amsterdam: Academic press. 1972. p. 286–291.
   Google Scholar
• Chiu C-W, Whistler RL. Alternate synthesis of 5-thio-d-glucose pentaacetate. J Org Chem. 1973;38:832–834.
   Google Scholar
• Gramera RE, Park A, Whistler RL. A convenient preparation of 1,2-mono-O-isopropylidene-α-d-glucofuranose1. J Org Chem. 1963;28:3230–3231.
   Google Scholar
• Meyer AS. Reichstein T. l-Idose aus d-glucose, sowie ein neuer Weg zur l-Idomethylose. Helv Chim Acta. 1946;29:152–162.
   Google Scholar
• Hedgley EJ, Mérész O, Overend WG. Structure and reactivity of anhydro-sugars. part VII. syntheses of 5-deoxy-d-xylo-hexose. J Chem Soc C: Org. 1967: 888–894.
   Google Scholar
• Rowell RM, Whistler RL. Derivatives of α-d-glucothiopyranose1. J Org Chem. 1966;31:1514–1516.
   Google Scholar
• Yuasa H, Tamura J-I, Hashimoto H. Synthesis of per-O-alkylated 5-thio-d-glucono-1,5-lactones and transannular participation of the ring sulphur atom of 5-thio-d-glucose derivatives on solvolysis under acidic conditions. J Chem Soc Perkin Trans. 1990;1:2763–2769.
   Google Scholar
• Abd El-Rahman MMA, Whistler RL. A shorter synthesis of 5-thio-α-d-glucose pentaacetate. Org Prep Proced Int. 1973;5:245–249.
   Google Scholar
• Driguez H, Henrissat B. A novel synthesis of 5-thio-d-glucose. Tetrahedron Lett. 1981;22:5061–5062.
   Google Scholar
• Owen LN, Peat S, Jones WJG. 65. Furanose and pyranose derivatives of glucurone. J. Chem Soc (Resumed). 1941: 339–344.
   Google Scholar
• Creighton AM, Owen LN. 211. Some carbohydrate episulphides. J Chem Soc (Resumed). 1960: 1024–1029.
   Google Scholar
• Hall LD, Hough L, Pritchard RA. 302. The epoxide–episulphide transformation. J Chem Soc (Resumed). 1961: 1537–1545.
   Google Scholar
• Hashimoto H, Kawanishi M, Yuasa H. Novel conversion of aldopyranosides into 5-thioaldopyranosides via acyclic monothioacetals with inversion and retention of configuration at C-5. Carbohydr Res. 1996;282:207–221.
   Google Scholar
• Hashimoto H, Kawanishi M, Yuasa H. New and facile synthetic routes to 5-thioaldohexopyranosides via aldose monothioacetal derivatives. Tetrahedron Lett. 1991;32:7087–7090.
   Google Scholar
• Guindon Y, Anderson PC. Stereoelectronic effects in the ring cleavage of methyl glycopyranosides using dimethylboron bromide. Tetrahedron Lett. 1987;28:2485–2488.
   Google Scholar
• Tsuda Y, Sato Y, Kanemitsu K, et al. Utilization of sugars in Organic synthesis. Part XXX. Thio-sugars. I. Radical-promoted thione-thiol rearrangement of cyclic thionocarbonates: synthesis of 5-Thioglucose.. Chem Pharm Bull. 1996;44:1465–1475.
   Google Scholar
• Tsuda Y, Noguchi S, Kanemitsu K, et al. Utilization of sugars in organic synthesis. Part XXXIII. Thio-sugars III. Radical catalyzed thione-thiol rearrangement of cyclic thionocarbonates on a pyranose ring: formation of cis-Arranged cyclic thiolcarbonates. Chem Pharm Bull. 1997;45:971–980.
   Google Scholar
• Uenishi JI, Ohmiya H. Novel synthesis of 5-thio-hexopyranoside: preparation of 5-thio-d- and l-glucose and 1,6-anhydro-5-thio-l- and d-altrose. Tetrahedron. 2003;59:7011–7022.
   Google Scholar
• Hyldtoft L, Madsen R. Carbohydrate carbocyclization by a novel zinc-mediated Domino reaction and ring-closing olefin metathesis. J Am Chem Soc. 2000;122:8444–8452.
   Google Scholar
• Uenishi JI, Motoyama M, Nishiyama Y, et al. Intramolecular ring opening of a 2,3-epoxy alcohol by a xanthate anionic center; stereospecific preparation of 2-mercapto-1,3-diol units. Heteroat Chem. 1994;5:51–60.
   Google Scholar
• Nam Shin JE, Perlin AS. Synthesis of 5-thio-d-galactose. Carbohydr Res. 1979;76:165–176.
   Google Scholar
• Wang Y, Du Y. Synthesis of 5-thio-d- galactopyranose. J Carbohydr Chem. 2013;32:240–248.
   Google Scholar
• Repetto E, Manzano VE, Uhrig ML, et al. Synthesis of branched dithiotrisaccharides via ring-opening reaction of sugar thiiranes. J Org Chem. 2012;77:253–265.
   Google Scholar
• Yuasa H, Izukawa Y, Hashimoto H. Synthesis of 5-thio-d-mannose. J Carbohydr Chem. 1989;8:753–763.
   Google Scholar
• Randall MH. Synthesis of methyl d-mannofufanosides and of 5-O-methyl-d-mannose. Carbohydr Res. 1969;11:173–178.
   Google Scholar
• Al-Masoudi NAL, Hughes NA. Synthesis of 5-thio-d-altrose and some of its derivatives. Carbohydr Res. 1986;148:39–49.
   Google Scholar
• Hughes NA. Synthesis of 5-thio-d-allose and 5-thio-d-altrose. J Chem Soc Chem Commun. 1979;7:319–320.
   Google Scholar
• Al-Masoudi NAL, Hughes NA. 5-Thiopyranoses. Part 12. Sulphur participation in displacement reactions of sulphonate esters of 5-thio-d-allose, 5-thio-d-altrose, and 5-thio-d-glucose derivatives. J Chem Soc Perkin Trans 1. 1987: 2061–2067.
   Google Scholar
• Al-Masoudi NAL, Hughes NA. 5-Thiopyranoses. Part 11. Isopropylidene acetals of 5-thio-d-glucose, 5-thio-d-allose, and 5-thio-d-altrose and some of their methyl glycosides. J Chem Soc Perkin Trans 1. 1987: 1413–1420.
   Google Scholar
• Al-Mosoudi NAL, Hughes NA. Synthesis of 5-thio-d-allose and the methyl 5-thio-α- and -β-d-allopyranosides. Carbohydr Res. 1986;148:25–37.
   Google Scholar
• Kovár J. Improvements for the preparation of l-idose from d-glucose. Can J Chem. 1970;48:2377–2385.
   Google Scholar
• Takahashi H, Hitomi Y, Iwai Y, et al. A novel and practical synthesis of l-hexoses from d-glycono-1,5-lactones. J Am Chem Soc. 2000;122:2995–3000.
   Google Scholar
• Takahashi H, Iwai Y, Hitomi Y, et al. Novel synthesis of l-ribose from d-mannono-1,4-lactone. Org Lett. 2002;4:2401–2403.
   Google Scholar
• Hollingsworth RI, Song X. A facile and general synthesis of rare l-sugar lactones. Synlett. 2007;2007:1247–1250.
   Google Scholar
• Lunau N, Meier C. Synthesis of l-altrose and some derivatives. European J Org Chem. 2012;2012:6260–6270.
   Google Scholar
• Kashem A, Anisuzzaman M, Whistler RL. 5-thio-l-rhamnose. Carbohydr Res. 1977;55:205–214.
   Google Scholar
• Denton RM, An J, Adeniran B, et al. Catalytic phosphorus(V)-mediated nucleophilic substitution reactions: development of a catalytic Appel reaction. J Org Chem. 2011;76:6749–6767.
   Google Scholar
• Appel R. Tertiary phosphane/tetrachloromethane, a versatile reagent for chlorination, dehydration, and P-N linkage. Ange Chem Int Edit Engl. 1975;14:801–811.
   Google Scholar
• Beynon PJ, Collins PM, Doganges PT, et al. The oxidation of carbohydrate derivatives with ruthenium tetroxide. J Chem Soc C: Org. 1966: 1131–1136.
   Google Scholar
• Adley T, Owen L. Thiosugars. Part I. The thiopyranose ring. J Chem Soc C: Org. 1966: 1287–1290.
   Google Scholar
• Hughes NA, Munkombwe NM, Todhunter ND. Synthesis of derivatives of 5-thio-l-idose. Carbohydr Res. 1992;216:119–128.
   Google Scholar
• Popsavin M, Popsavin V, Vukojević N, et al. Preparation of 2, 5-anhydro-3, 4, 6-tri-O-benzoyl-d-allononitrile from d-glucose. Carbohydr Res. 1994;260:145–150.
   Google Scholar
• Augé J, David S. Hexopyranose sugars conformation revised. Tetrahedron. 1984;40:2101–2106.
   Google Scholar
• Calvo-Flores FG, García-Mendoza P, Hernández-Mateo F, et al. Applications of cyclic sulfates of vic-diols: synthesis of episulfides, olefins, and thio sugars. J Org Chem. 1997;62:3944–3961.
   Google Scholar
• Gao Y, Sharpless KB. Vicinal diol cyclic sulfates. Like epoxides only more reactive. J Am Chem Soc. 1988;110:7538–7539.
   Google Scholar
• Lambert JB, Wharry SM. Conformational analysis of 5-thio-d-glucose. J Org Chem. 1981;46:3193–3196.
   Google Scholar
• Emery F, Vogel P. Total asymmetric synthesis of 5-deoxy-5-thio-l-allose. J Carbohydr Chem. 1994;13:555–563.
   Google Scholar
• Vieira E, Vogel P. The preparation of optically pure 7-oxabicyclo [2.2.1]hept-2-ene derivatives. The CD spectrum of (+)-(1R)-7-Oxabicyclo [2.2.1]hept-5-en-2-one. Helv Chim Acta. 1983;66:1865–1871.
   Google Scholar
• Vogel P. Synthesis of rare carbohydrates and biomolecules from furan. Bulletin des Sociétés Chimiques Belges. 1990;99:395–439.
   Google Scholar
• Reymond J-L, Vogel P. New chiral auxiliaries and new optically pure ketene equivalents derived from tartaric acids. Improved synthesis of (−)-7-oxabicyclo [2.2. 1] hept-5-en-2-one. Tetrahedron: Asymmetry. 1990;1:729–736.
   Google Scholar
• Auberson Y, Vogel P. Total synthesis of l-allose, l-talose, and derivatives. Helv Chim Acta. 1989;72:278–286.
   Google Scholar
• Izumi M, Tsuruta O, Hashimoto H. A facile synthesis of 5-thio-l-fucose and 5-thio-d-arabinose from d-arabinose. Carbohydr Res. 1996;280:287–302.
   Google Scholar
• Hashimoto H, Izumi M. A facile synthesis of 5-thio-l-fucose and 3-O-allyl-l-fucose triacetate from d-arabinose. Chem Lett. 1992;21:25–28.
   Google Scholar
• Fuller T, Stick R. Further stereoselective reductions of 3-O-hexofuranosyl S-methyl dithiocarbonates with tributyltin deuteride. A comment on mechanism. Aust J Chem. 1980;33:2509–2515.
   Google Scholar
• Aguirre-Valderrama A, Dobado JA. Conformational analysis of thiosugars: theoretical NMR chemical shifts and 3 JH, H coupling constants of 5-thio-pyranose monosaccharides. J Carbohydr Chem. 2006;25:557–594.
   Google Scholar
• Horton D, Varela O. Crystalline 2,3:4,5-di-O-isopropylidene-dl-arabinose diethyl dithioacetal: some reactions of acetal derivatives of arabinose. Carbohydr Res. 1984;134:205–214.
   Google Scholar
• Omura K, Swern D. Oxidation of alcohols by “activated” dimethyl sulfoxide. A preparative, steric and mechanistic study. Tetrahedron. 1978;34:1651–1660.
   Google Scholar
• Corey EJ, Suggs JW. Selective cleavage of allyl ethers under mild conditions by transition metal reagents. J Org Chem. 1973;38:3224–3224.
   Google Scholar
• Gigg R, Warren CD. The allyl ether as a protecting group in carbohydrate chemistry. part II. J Chem Soc C: Org. 1968: 1903–1911.
   Google Scholar
• Cleland WW. Dithiothreitol, a new protective reagent for SH groups. Biochemistry. 1964;3:480–482.
   Google Scholar
• Takahashi S, Kuzuhara H. Syntheses of l-fucopyranose and its homologs with ring heteroatoms other than oxygen. Stereocontrolled conversion of a common d-arabinofuranoside intermediate. Chem Lett. 1992;21:21–24.
   Google Scholar
• Fujita K, Ohta K, Ikegami Y, et al. General method for preparing altrosides from 2, 3-manno-epoxides and its application to synthesis of alternative β-cyclodextrin with an altroside as the constituent of macrocyclic structure. Tetrahedron Lett. 1994;35:9577–9580.
   Google Scholar
• Ingles DL, Whistler RL. Preparation of several methyl d-pentothiapyranosides1. J Org Chem. 1962;27:3896–3898.
   Google Scholar
• Rao VSR, Foster JF, Whistler RL. Ring conformation in methyl α- and β-d-xylothiapyranosides as demonstrated by nuclear magnetic resonance1. J Org Chem. 1963;28:1730–1731.
   Google Scholar
• Moravcová J, Čapková J, Staněk J. One-pot synthesis of 1,2-O-isopropylidene-α-d-xylofuranose. Carbohydr Res. 1994;263:61–66.
   Google Scholar
• Moravcová J, Čapková J, Staněk J, et al. Methyl 5-deoxy-α and β-d-xylofuranosides. J Carbohydr Chem. 1997;16:1061–1073.
   Google Scholar
• Bozó É, Boros S, Kuszmann J, et al. An economic synthesis of 1, 2, 3, 4-tetra-O-acetyl-5-thio-d-xylopyranose and its transformation into 4-substituted-phenyl 1, 5-dithio-d-xylopyranosides possessing antithrombotic activity. Carbohydr Res. 1998;308:297–310.
   Google Scholar
• Lalot J, Stasik I, Demailly G, et al. Efficient synthesis of 5-thio-d-arabinopyranose and 5-thio-d-xylopyranose from the corresponding d-pentono-1, 4-lactones. Carbohydr Res. 2003;338:2241–2245.
   Google Scholar
• Lalot J, Stasik I, Demailly G, et al. An improved synthesis of 5-thio-d-ribose from d-ribono-1, 4-lactone. Carbohydr Res. 2002;337:1411–1416.
   Google Scholar
• Bouchez V, Stasik I, Beaupère D, et al. Regioselective halogenation of pentono-1,4-lactones. Efficient synthesis of 5-chloro- and 5-bromo-5-deoxy derivatives. Carbohydr Res. 1997;300:139–142.
   Google Scholar
• Charmantray F, Dellis P, Hélaine V, et al. Chemoenzymatic synthesis of 5-thio-d-xylopyranose. European J Org Chem. 2006;2006:5526–5532.
   Google Scholar
• André C, Guérard C, Hecquet L, et al. Modified l-threose and d-erythrose as substrates of transketolase and fructose-1, 6-bisphosphate aldolase. Application to the synthesis of new heptulose analogues. J Mol Catal B: Enzym. 1998;5:459–466.
   Google Scholar
• Espelt L, Parella T, Bujons J, et al. Stereoselective aldol additions catalyzed by dihydroxyacetone phosphate-dependent aldolases in emulsion systems: preparation and structural characterization of linear and cyclic iminopolyols from aminoaldehydes. Chem–A Eur J. 2003;9:4887–4899.
   Google Scholar
• El Blidi L, Crestia D, Gallienne E, et al. A straightforward synthesis of an aminocyclitol based on an enzymatic aldol reaction and a highly stereoselective intramolecular Henry reaction. Tetrahedron: Asymmetry. 2004;15:2951–2954.
   Google Scholar
• Zimmermann FT, Schneider A, Schörken U, et al. Efficient multi-enzymatic synthesis of d-xylulose 5-phosphate. Tetrahedron: Asymmetry. 1999;10:1643–1646.
   Google Scholar
• Kobori Y, Myles DC, Whitesides GM. Substrate specificity and carbohydrate synthesis using transketolase. J Org Chem. 1992;57:5899–5907.
   Google Scholar
• Guérard C, Alphand V, Archelas A, et al. Transketolase-mediated synthesis of 4-deoxy-d-fructose 6-phosphate by epoxide hydrolase-catalysed resolution of 1, 1-diethoxy-3, 4-epoxybutane. European J Org Chem. 1999;1999:3399–3402.
   Google Scholar
• Crestia D, Guérard C, Veschambre H, et al. Chemoenzymatic synthesis of chiral substituted acrylate and acrylonitrile precursors for the synthesis of 3-deoxy-2-ulosonic acids and α-methylene-γ-lactones. Tetrahedron: Asymmetry. 2001;12:869–876.
   Google Scholar
• Liu Z, Sayre LM. Model studies on the modification of proteins by lipoxidation-derived 2-hydroxyaldehydes. Chem Res Toxicol. 2003;16:232–241.
   Google Scholar
• Effenberger F, Straub A, Null V. Enzym-katalysierte Reaktionen, 14. Stereoselektive Darstellung von Thiozuckern aus achiralen Vorstufen mittels Enzymen. Liebigs Ann Chem. 1992;1992:1297–1301.
   Google Scholar
• Ouwerkerk N, Steenweg M, De Ruijter M, et al. One-pot two-step enzymatic coupling of pyrimidine bases to 2-deoxy-d-ribose-5-phosphate. A new strategy in the synthesis of stable isotope labeled deoxynucleosides. J Org Chem. 2002;67:1480–1489.
   Google Scholar
• Ferroni EL, DiTella V, Ghanayem N, et al. A three-step preparation of dihydroxyacetone phosphate dimethyl acetal. J Org Chem. 1999;64:4943–4945.
   Google Scholar
• Chou W-C, Chen L, Fang J-M, et al. A new route to deoxythio sugars based on aldolases. J Am Chem Soc. 1994;116:6191–6194.
   Google Scholar
• Hughes NA, Munkombwe NM. Synthesis of 5-thio-d-arabinose and 5-thio-d-lyxose and their methyl glycopyranosides. Carbohydr Res. 1985;136:397–409.
   Google Scholar
• Whistler RL, Rowell RM. Preparation of methyl l-arabinothiapyranoside and disulfide derivatives of 5-Mercapto-l-arabinose1. J Org Chem. 1964;29:1259–1261.
   Google Scholar
• Kam BL, Oppenheimer NJ. Selective tritylation: a general, one-step, method for synthesis of 5-O-trityl-d-pentofuranoses. Carbohydr Res. 1979;69:308–310.
   Google Scholar
• Clayton CJ, Hughes NA. 5-thio-d-ribopyranose: part I. The free sugar and the methyl glycosides. Carbohydr Res. 1967;4:32–41.
   Google Scholar
• Leonard NJ, Carraway KL. 5-Amino-5-deoxyribose derivatives. Synthesis and use in the preparation of “reversed” nucleosides. J Heterocycl Chem. 1966;3:485–489.
   Google Scholar
• Clayton CJ, Hughes NA. 5-thio-d-ribopyranose: part II. Methyl, 1,5-dithio-d-ribopyranosides. Carbohydr Res. 1973;27:89–95.
   Google Scholar
• Hughes NA. 5-thio-d-ribopyranose: part III. Conformational equilibria in the methyl d-ribopyranosides, their 1-thio, 5-thio, and 1,5-dithio analogues, and the related triacetates. Carbohydr Res. 1973;27:97–105.
   Google Scholar
• Fleetwood A, Hughes NA. Convenient synthesis of 2,3-O-isopropylidene-5-thio-d-ribose and 5-thio-d-ribose; synthesis of 1,4-anhydro-2,3-O-isopropylidene-α-d-ribopyranose and 1,4-anhydro-2,3-O-isopropylidene-5-thio-α-d-ribopyranose. Carbohydr Res. 1999;317:204–209.
   Google Scholar
• Bozó É, Boros S, Kuszmann J. Synthesis of 4-cyanophenyl and 4-nitrophenyl 1,5-dithio-d-ribopyranosides as well as their 2-deoxy and 2,3-dideoxy derivatives possessing antithrombotic activity. Carbohydr Res. 1999;321:52–66.
   Google Scholar
• Lerner LM. Enantiomeric forms of 9-(5-deoxy-β-erythro-pent-4-enofuranosyl)adenine and a new preparation of 5-deoxy-d-lyxose. Carbohydr Res. 1977;53:177–185.
   Google Scholar
• Hughes NA, Wood CJ. Isopropylidene acetals of 5-Thiopentopyranoses. Carbohydr Res. 1976;49:225–232.
   Google Scholar
• Bozó É, Kuszmann J. Synthesis of 4-cyanophenyl and 4-nitrophenyl 2-azido-2-deoxy-1, 5-dithio-β-d-arabino-and-β-d-lyxopyranosides possessing antithrombotic activity. Carbohydr Res. 2000;325:143–149.
   Google Scholar
• Renaut P, Millet J, Sepulchre C, et al. 5a-Carba-β-d-, 5a-carba-β-l-and 5-thio-β-l-xylopyranosides as new orally active venous antithrombotic agents. Helv Chim Acta. 1998;81:2043–2052.
   Google Scholar
• Martin NB, Masson P, Sepulchre C, et al. Pharmacologic and biochemical profiles of new venous antithrombotic β-d-xyloside derivatives: potential antiathero/thrombotic drugs. Semin Thromb Hemost. 1996;22:247–254.
   Google Scholar
• Bozo E, Boros S, Kuszmann J. Synthesis of 4-cyanophenyl and 4-nitrophenyl 1, 5-dithio-l-and-d-arabinopyranosides possessing antithrombotic activity. Carbohydr Res. 1998;311:191–202.
   Google Scholar
• Norris P, Horton D, Levine BR. Synthesis of 1, 5-dideoxy-1, 5-imino-d-xylonolactam VIA acid-catalyzed intramolecular schmidt rearrangement. Tetrahedron Lett. 1995;36:7811–7814.
   Google Scholar
• Hughes NA, Munkombwe NM. Formation of methyl 5-thiopentopyranosides in the d-arabino, l-lyxo, d-ribo, and d-xylo series from methyl 5-thio-3-O-toluene-p-sulphonyl-α-d-xylopyranoside. Carbohydr Res. 1985;136:411–418.
   Google Scholar
• Hull DMC, Orchard PF, Owen LN. Thiosugars. Part 8. Methyl 2,3-anhydro-5-thio-α-d-ribopyranoside and methyl 3,4-anhydro-5-thio-α-d-ribopyranoside. J Chem Soc Perkin Trans 1. 1977: 1234–1239.
   Google Scholar
• Karrer P, Boettcher A. Neue synthese der d-xylomethylose. Helv Chim Acta. 1953;36:837–838.
   Google Scholar
• Takeda A, Watanabe T, Katsumata T, et al. Thiopyranose compound and method for producing same. U.S. Patent 9,815,812, November 14, 2017.
   Google Scholar
• Bock K, Thøgersen H. Nuclear magnetic resonance spectroscopy in the study of mono- and oligosaccharides. In: Webb GA, editor. Annual reports on NMR spectroscopy. Vol. 13. Amsterdam: Academic Press; 1983. p. 1–57.
   Google Scholar
• Bock K, Pedersen C. Carbon-13 nuclear magnetic resonance spectroscopy of monosaccharides. In: Tipson RS, Horton D, editor. Advances in carbohydrate chemistry and biochemistry. Vol. 41. Amsterdam: Academic Press; 1983. p. 27–66.
   Google Scholar
• Duus JØ, Gotfredsen CH, Bock K. Carbohydrate structural determination by NMR spectroscopy: modern methods and limitations. Chem Rev. 2000;100:4589–4614.
   Google Scholar