149
Views
1
CrossRef citations to date
0
Altmetric
Articles

Glycosyl hydroperoxides

, , &
Pages 104-116 | Received 29 Dec 2017, Accepted 27 Jan 2018, Published online: 08 Mar 2018

References

  • Berkessel, A.; Vogl, N. Synthetic uses of peroxides; in The chemistry of peroxides Rappoport; Z. (Ed.), Vol. 2, Part 1, John Wiley & Sons Ltd, 2006, 307–596.
  • Dussault, P. Reactions of hydroperoxides and peroxides; in Active Oxygen in Chemistry. In Foote, Ch.S.; Valentine, J.S; Greenberg, A.; Liebman, J.F. Eds., Blackie Academic & Professional 1995, 141–203.
  • Mieczkowski, J.; Jurczak, J.; Chmielewski, M.; Zamojski, A. The Synthesis of 2,3-Dideoxyhex-2-Enono-1,5-Lactones. Carbohydr. Res. 1977, 56, 180–182.
  • Rieche, A.; Bischoff, C. Alkylperoxyde, XXVI. Die Umacetalisierung von Acetalen mit Wasserstoffperoxyd, eine Allgemein Anwendbare Methode zur Darstellung von α-Hydroperoxy-dialkyläthern (Ätherhydroperoxyde). Chem. Ber. 1961, 94, 2722–2726.
  • Chmielewski, M.; Jurczak, J.; Maciejewski, S. Stable, Enantiomerically pure Hydroperoxides Derived from Sugars. Carbohydr. Res. 1987, 165, 111–115.
  • Ferrier, R. J.; Zubkov, O. A. Transformation of Glycals into 2,3-Unsaturated Glycosyl Derivative. Organic Reactions 2003, 62, 569–736.
  • Mostowicz, D.; Jurczak, M.; Hamann, H.-J.; Höft, E.; Chmielewski, M. Oxydation of Glycals with Hydrogen Peroxide. Eur. J. Org. Chem. 1998, 2617–2621.
  • Fehlhaber, H.-W.; Snatzke, G.; Vlahov, I. Synthese von 1α-Hydroperoxy-Zuckerderivaten. Liebigs Ann. Chem. 1987, 637–638.
  • Dwyer, C. L.; Gill, C. D.; Ichihara, O.; Taylor, R. J. K. The Enantioselective Epoxidation of Quinones using Sugar Hyperoxides. Synlett 2000, 704–706.
  • Bundu, A.; Berry, N. G.; Gill, C. D.; Dwyer, C. L.; Stachulski, A. V.; Taylor, R. J. K.; Whittall, J. The Design and Synthesis of Novel Anomeric Hydroperoxides: influence of the Carbohydrate Residue in the Enantioselective Epoxidation of Quinones. Tetrahedron: Asymmetry 2005, 16, 283–293.
  • Booma, C.; Balasubramanian, K. K. A New Ferrier system: 2-C Acetoxymethylglycals. A Convenient entry to 2-C-Methylene Glycosides. J. Chem. Soc. Chem. Commun. 1993, 1394–1395.
  • Ramesh, N. G.; Balasubramanian, K. K. Mitsunobu Reaction of 1,5-anhydro-3,4,6-tri-O-Benzyl-2- deoxy-2-Hydroxymethyi-hex-l-Enitols and 1,5-anhydro-2-deoxy- 4,6-O-Protected-hex-l-enitols. A Novel method for the Synthesis of 2-C-Methylene Glycosides and an Useful Alternative to Ferrier Rearrangement. Tetrahedron 1995, 51, 255–272.
  • Hamann, H.-J.; Höft, E.; Mostowicz, D.; Mishnev, A.; Urbańczyk-Lipkowska, Z.; Chmielewski, M. New optically Pure Sugar Hydroperoxides. Synthesis and use for Enantioselective Oxygen Transfer. Tetrahedron 1997, 53, 185–192.
  • Kośnik, W.; Stachulski, A.; Chmielewski, M. New Stable Anomeric Hydroperoxides Derived from 2-Deoxy-Sugars; Enantioselective Epoxidation of 2-methyl-1,4-Naphtoquinone. Tetrahedron: Asymmetry 2005, 16, 1975–1981. Corrigendum, Tetrahedron: Asymmetry 2006, 17, 313.
  • Szechner, B.; Urbańczyk-Lipkowska, Z.; Chmielewski, M. Glycosyl Hydroperoxides Derived from 2-Deoxysugars. Carbohydr. Res. 2010, 345, 2464–2468.
  • Milas, N. A.; Sussman, S. J. The Hydroxylation of the Double Bond. J. Am. Chem. Soc. 1936, 58, 1302–1304.
  • Mąkosza, M.; Surowiec, M. Chloromethyl Methyl Sulfone by Oxidation of Chloromethyl Methylsulfide. OPPI Briefs' 2003, 35, 412–414.
  • Kośnik, W.; Bocian, W.; Chmielewski, M.; Tvaroška, I. DFT Calculations of the Anomeric and Exo-Anomeric Effect of the Hydroperoxy and Peroxy Groups. Carbohydr. Res. 2008, 343, 1463–1472.
  • Dussault, P. H.; Woller, K. R. Singlet Oxygenation Radical Rearrangement as an Approach to 1,4-Dioxygenated Peroxides: Asymmetric total Syntheses of Plakorin and enantio-Chondrillin. J. Am. Chem. Soc. 1997, 119, 3824–3825.
  • Kośnik, W.; Grzeszczyk, B.; Chmielewski, M. Bis-Glycosyl Peroxides. Synlett 2007, 2837–2840.
  • a) Schulz, M.; Steinmaus, H. Neuer Abbau von Glucose zu Arabinose. Angew. Chem. 1963, 75, 918. b) Schulz, M.; Boeden, H. Synthese von Acetylierten Peroxy-glycosiden der D-Mannose und L-Rhamnose. Tetrahedron Lett. 1966, 25, 2843–2848.
  • Nicolaou, K. C.; Chucholowski, A.; Dolle, R. E.; Randall, J. L. Reactions of Glycosyl Fluorides. Synthesis of O-, S-, and N-glycosides. J. Chem. Soc., Chem. Commun. 1984, 1155–1156.
  • Szechner, B.; Furman, B.; Chmielewski, M. Glycosyl Hydroperoxides. Carbohydr. Res. 2013, 369, 54–57.
  • Kumar, A.; Kumar, V.; Dere, R. T.; Schmidt, R. R. Glycoside Bond Formation via Acid–Base Catalysis. Org. Lett. 2011, 13, 3612–3615.
  • Katsuki, T.; Martin, V. S. Asymmetric Epoxidation of Allylic Alkohols: the Katsuki-Sharpless Epoxidation Reaction. Organic Reactions 1996, 48, 1–299.
  • Jacobsen, E. N. Asymmetric Catalytic Epoxidation of Unfunctionalized Olefins. In Catalytic Asymmetric Synthesis, Ojima I. (Ed) VCH, New York, 1993, 159–202.
  • (a) Adam, W.; Fell, T. R.; Hoch, U.; Saha-Möller, C. R.; Schreier, P. Kinetic Resolution of Chiral α-Hydroperoxy Esters by Horseradish Peroxidase-Catalyzed Enantioselective Reduction to α-Hydroxy Esters. Tetrahedron: Asymmetry 1995, 6, 1047–1050. (b) Adam, W.; Hoch, U.; Lazarus, M.; Saha-Möller, C. R.; Schreier, P. Enzyme-Catalyzed Asymmetric Synthesis: Kinetic Resolution of Racemic Hydroperoxides by Enantioselective Reduction to Alcohols with Horseradish Peroxidase and Guiacol. J. Am. Chem. Soc. 1995, 117, 11898–11901.
  • Hamann, H. J.; Höft, E.; Chmielewski, M.; Maciejewski, S. Enantioselective Epoxidation by an Optically active Hydroperoxide. Chirality 1990, 5, 338–340.
  • Finn, M. G.; Sharpless, K. B. On the Mechanism of Asymmetric Epoxidation with Titanium-Tartrate Catalysts. In Asymmetric Synthesis, J. D. Morrison ed.; Academic Press: New York, 1985; Vol. 5, pp 247–308.
  • Hamann, H.-J.; Chmielewski, M.; Mostowicz, D.; Liebscher, J. Enantioselective Epoxidation of 1-Hexene with Sugar Derived Hydroperoxides. ARKIVOC 2007, (ix), 17–20.
  • (a) Fraser-Reid, B.; Radatus, B. J. 4,6-Di-O-acetyl-Aldehydo-2,3-Dideoxy-D-Erythro-trans-hex-2-enose. Probable reason for the ‘al’ in Emil Fischer's Triacetyl glucal. J. Am. Chem. Soc. 1970, 92, 5288–5290. (b) Gonzales, F.; Lesage, S.; Perlin, A. S. Catalysis by Mercuric Ion of Reactions of Glycals with Water. Carbohydr. Res. 1975, 42, 267–274. (c) Torsel, K.; Tyagi, M. P. Reaction of Parasorbic Acid. Synthesis of 2-Alkoxy-5,6-dihydro-α-pyrans and D,L – Osmunda Lactone. Acta Chem. Scand. 1977, B 31, 297–301. (d) Tatsuta, K.; Yamauchi, T.; Kinoshita, M. Stereospecific Synthesis of the C-9 – C-16 Segment of Carbonolide B, the Aglycon of Carbomycin B. Bull. Chem. Soc. Japan 1978, 51, 3035–3038. (e) Chmielewski, M. Butyl (E)-2-Hydroxy-6-oxo-hex-4- Enoate a Novel Substrate for total Synthesis of Deoxy-Sugars. Polish J. Chem. 1980, 54, 1913–1921.
  • Kośnik, W.; Bocian, W.; Kozerski, L.; Tvaroška, I.; Chmielewski, M. Enantioselective Epoxidation of Electrophilic Olefins Using Glycosyl Hydroperoxides. Chem. Eur. J. 2008, 14, 6087–6097.
  • (a) Hien, T. T.; White, N. J. Qinghaosu. Lancet 1993, 341, 603–608. (b) Meshnick, S. R.; Taylor, T. E.; Kamchonwongpaisan, S. Artemisin and the Antimalarial Endoperoxides: from Herbal Remedy to Targeted Chemotherapy. Microbiol. Rev. 1996, 60, 301–315. (c) Zhou, W. S.; Xu, X. X. Total Synthesis of the Antimalarial Sesquiterpene Peroxide Qinghaosu and Yingzhaosu A. Acc. Chem. Res. 1994, 27, 211–216. (d) Haynes, R. K.; Vonwiller, S. C. From Qinghao, Marvelous herb of Antiquity, to the Antimalarial Trioxane Qinghaosu – and some Remarkable New Chemistry. Acc. Chem. Res. 1997, 30, 73–79. (e) Cumming, J. N.; Ploypradith, P.; Posner, G. H. Antimalarial Activity of Artemisinin (Qinghaosu) and Related Trioxanes: Mechanism of Action. Adv. Pharmacol. 1996, 37, 253–297.
  • (a) Posner, G. H.; O'Dowd, H.; Ploypradith, P.; Cumming, J. N.; Suji, X.; Shapiro, T. A. Antimalarial Cyclic peroxy Ketals. J. Med. Chem. 1998, 41, 2164–2167. (b) Schobert, R.; Stehle, R.; Milius, W. Hydroperoxide and Endoperoxide Lactones from Photooxygenation of 3-Alkylidenedihydrofuran-2,4-Diones. J. Org. Chem. 2003, 68, 9827–9830. (c) Cetin, F.; Yenil, N.; Yüceer, L. Stable Spiro-Endoperoxides by Sunlight-Mediated Photooxygenation of 1,2-O-Alkylidene-5(E)-eno-5,6,8-Trideoxy-a-D-xylo-oct-1,4-Furano-7-Uloses. Carbohydr. Res. 2005, 340, 2583–2589. (d) Dussault, P. H.; Han, Q.; Sloss, D. G.; Symonsbergen, D. J. Photooxygenation of Chiral Dienol Ethers: Asymmetric Synthesis of Alkoxydioxines. Tetrahedron 1999, 55, 11437–11454. (e) Gavrilan, M.; Andre-Barrès, C.; Baltas, M.; Tzedakis, T.; Gorrichon, L. Bicyclic Peroxides in the G Factors Series: Synthesis and Electrochemical Studies. Tetrahedron Lett. 2001, 42, 2465–2468.
  • Szechner, B.; Jaromin, A.; Parapini, S.; Basilico, N.; Grzeszczyk, B.; Furman, B.; Chmielewski, M. Glycosyl Hydroperoxides a new class of Potential Antimalarial Agents. Bioorg. Med. Chem. 2015, 23, 3033–3039.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.