In Situ Preactivation Strategies for the Expeditious Synthesis of Oligosaccharides: A Review

REFERENCES

• Dwek, R.A.; Butters, T.D.; Platt, F.M.; Zitzmann, N. Targeting glycosylation as a therapeutic approach. Nat. Rev. Drug Discovery 2002, 1, 65.
   PubMed Web of Science ®Google Scholar
• Kilcoyne, M.; Joshi, L. Carbohydrates in therapeutics. Cardiovasc. Hematol. Agents Med. Chem. 2007, 5, 186.
   PubMedGoogle Scholar
• Nogueira, C.M.; Parmanhan, B.R.; Farias, P.P.; Correa, A.G. The increasing importance of carbohydrates in medicinal chemistry. Rev. Virtual Quim. 2009, 1, 149.
   Google Scholar
• Cipolla, L.; Araujo, A.C.; Bini, D.; Gabrielli, L.; Russo, L.; Shaikh, N. Discovery and design of carbohydrate-based therapeutics. Expert Opin. Drug Discovery 2010, 5, 721.
   PubMed Web of Science ®Google Scholar
• Bertran-Vicente, J.; Hackenberger, C.P. R. A supramolecular peptide synthesizer. Angew. Chem., Int. Ed. 2013, 52, 6140.
   PubMed Web of Science ®Google Scholar
• Tanaka, T.; Letsinger, R.L. Syringe method for stepwise chemical synthesis of oligonucleotides. Nucleic Acids Research 1982, 10, 3249.
   PubMed Web of Science ®Google Scholar
• Smoot, J.T.; Demchenko, A.V., Oligosaccharide synthesis: From conventional methods to modern expeditious strategies. In Advances in Carbohydrate Chemistry and Biochemistry, Derek, H., Ed. Academic Press: Washington, DC, 2009; Vol. 62, pp. 161.
   Google Scholar
• Huang, X.; Wang, Z., Strategies in oligosaccharide synthesis. In Comprehensive Glycoscience, Kamerling, H., Ed. Elsevier: Oxford, 2007; pp 379–413.
   Google Scholar
• Aoki, S.; Kondo, H.; Wong, C.-H. Glycosyl phosphites as glycosylation reagents. Methods Enzymol. 1994, 247, 193.
   PubMed Web of Science ®Google Scholar
• Backinowsky, L.V.; Abronina, P.I.; Shashkov, A.S.; Grachev, A.A.; Kochetkov, N.K.; Nepogodiev, S.A.; Stoddart, J.F. An efficient approach towards the convergent synthesis of “fully-carbohydrate” mannodendrimers. Chem. - Eur. J. 2002, 8, 4412.
   PubMed Web of Science ®Google Scholar
• Fraser-Reid, B.; Udodong, U.E.; Wu, Z.; Ottosson, H.; Merritt, J.R.; Rao, C.S.; Roberts, C.; Madsen, R. n-Pentenyl glycosides in organic chemistry: A contemporary example of serendipity. Synlett 1992, 927.
   Web of Science ®Google Scholar
• Demchenko, A.; Boons, G.-J. A highly convergent synthesis of a hexasaccharide derived from the oligosaccharide of group B type III Streptococcus. Tetrahedron Lett. 1997, 38, 1629.
   Web of Science ®Google Scholar
• Demchenko, A.V.; Boons, G.-J. A highly convergent synthesis of a complex oligosaccharide derived from group B type III Streptococcus. J. Org. Chem. 2001, 66, 2547.
   PubMed Web of Science ®Google Scholar
• Plante, O.J.; Palmacci, E.R.; Seeberger, P.H. Automated solid-phase synthesis of oligosaccharides. Science 2001, 291, 1523.
   PubMed Web of Science ®Google Scholar
• Yamago, S.; Yamada, T.; Hara, O.; Ito, H.; Mino, Y.; Yoshida, J.-i. A new, iterative strategy of oligosaccharide synthesis based on highly reactive β-bromoglycosides derived from selenoglycosides. Org. Lett. 2001, 3, 3867.
   PubMed Web of Science ®Google Scholar
• Mehta, S.; Pinto, B.M. Novel glycosidation methodology. The use of phenyl selenoglycosides as glycosyl donors and acceptors in oligosaccharide synthesis. J. Org. Chem. 1993, 58, 3269.
   Web of Science ®Google Scholar
• Mehta, S.; Pinto, B.M. Phenylselenoglycosides as novel, versatile glycosyl donors. Selective activation over thioglycosides. Tetrahedron Lett. 1991, 32, 4435.
   Web of Science ®Google Scholar
• Zuurmond, H.M.; van der Meer, P.H.; van der Klein, P.A. M.; van der Marel, G.A.; van Boom, J.H. Iodonium-promoted glycosylations with phenyl selenoglycosides. J. Carbohydr. Chem. 1993, 12, 1091.
   Web of Science ®Google Scholar
• Baeschlin, D.K.; Chaperon, A.R.; Charbonneau, V.; Green, L.G.; Ley, S.V.; Lucking, U.; Walther, E. Rapid assembly of oligosaccharides: total synthesis of a glycosylphosphatidylinositol anchor of Trypanosoma brucei. Angew. Chem., Int. Ed. 1999, 37, 3423.
   Web of Science ®Google Scholar
• Demchenko, A.V.; Kamat, M.N.; De Meo, C. S-benzoxazolyl (SBox) glycosides in oligosaccharide synthesis: Novel glycosylation approach to the synthesis of β-D-glucosides, β-D-galactosides, and α-D-mannosides. Synlett 2003, 1287.
   Web of Science ®Google Scholar
• Demchenko, A.V.; Malysheva, N.N.; De Meo, C. S-Benzoxazolyl (SBox) glycosides as novel, versatile glycosyl donors for stereoselective 1,2-cis glycosylation. Org. Lett. 2003, 5, 455.
   PubMed Web of Science ®Google Scholar
• Demchenko, A.V.; Pornsuriyasak, P.; De Meo, C.; Malysheva, N.N. Potent, versatile, and stable: thiazolyl thioglycosides as glycosyl donors. Angew. Chem., Int. Ed. 2004, 43, 3069.
   PubMed Web of Science ®Google Scholar
• Pornsuriyasak, P.; Demchenko, A.V. Glycosyl thioimidates in a highly convergent one-pot strategy for oligosaccharide synthesis. Tetrahedron: Asymmetry 2005, 16, 433.
   Web of Science ®Google Scholar
• Kochetkov, N.K.; Malysheva, N.N.; Klimov, E.M.; Demchenko, A.V. Synthesis of polysaccharides with 1,2-cis-glycosidic linkages by trityl-thiocyanate polycondensation. Stereoregular α-(1→6)-D-glucan. Tetrahedron Lett. 1992, 33, 381.
   Web of Science ®Google Scholar
• Codée, J.D. C.; van den Bos, L.J.; Litjens, R.E. J. N.; Overkleeft, H.S.; Van Boom, J.H.; van der Marel, G.A. Sequential one-pot glycosylations using 1-hydroxyl and 1-thiodonors. Org. Lett. 2003, 5, 1947.
   PubMed Web of Science ®Google Scholar
• Codée, J.D. C.; Litjens, R.E. J. N.; den Heeten, R.; Overkleeft, H.S.; van Boom, J.H.; van derMarel, G.A. Ph2SO/Tf2O: A powerful promotor system in chemoselective glycosylations using thioglycosides. Org. Lett. 2003, 5, 1519.
   PubMed Web of Science ®Google Scholar
• Hanessian, S.; Huynh, H.K.; Reddy, G.V.; Duthaler, R.O.; Katopodis, A.; Streiff, M.B.; Kinzy, W.; Oehrlein, R. Synthesis of Gal determinant epitopes, their glycomimetic variants, and trimeric clusters-relevance to tumor associated antigens and to discordant xenografts. Tetrahedron 2001, 57, 3281.
   Web of Science ®Google Scholar
• Lou, B.; Eckhardt, E.; Hanessian, S. Oligosaccharide synthesis by selective anomeric activation with MOP- and TOPCAT-leaving groups. In Preparative Carbohydrate Chemistry, Dekker: New York, 1997; pp 449.
   Google Scholar
• Lou, B.; Reddy, G.V.; Wang, H.; Hanessian, S. Glycoside and oligosaccharide synthesis with unprotected glycosyl donors based on the remote activation concept. In Preparative Carbohydrate Chemistry, Dekker: New York, 1997; pp 389.
   Google Scholar
• Nitz, M.; Bundle, D.R. Glycosyl halides in oligosaccharides synthesis. In Glycoscience: Chemistry and Chemical Biology I-III. Springer-Verlag: Berlin, 2001; pp 1497.
   Google Scholar
• Igarashi, K. The Koenigs-Knorr reaction. Adv. Carbohydr. Chem. Biochem. 1977, 34, 243.
   Google Scholar
• Schmidt, R.R.; Jung, K.-H. Trichloroacetimidates. In Carbohydrates in Chemistry and Biology, Wiley-VCH Verlag GmbH: Weinheim, 2000; pp 5.
   Google Scholar
• Ziegler, T.; Eckhardt, E.; Birault, V. Synthetic studies toward pyruvate acetal containing saccharides. Synthesis of the carbohydrate part of the Mycobacterium smegmatis pentasaccharide glycolipid and fragments thereof for the preparation of neoantigens. J. Org. Chem. 1993, 58, 1090.
   Web of Science ®Google Scholar
• Yamada, H.; Harada, T.; Takahashi, T. Synthesis of an Elicitor-active hexaglucoside analog by a one-pot, two-step glycosidation procedure. J. Am. Chem. Soc. 1994, 116, 7919.
   Web of Science ®Google Scholar
• Nicolaou, K.C.; Ueno, H. Oligosaccharide synthesis from glycosyl fluorides and sulfides. In Preparative Carbohydrate Chemistry, Dekker: New York, 1997; pp 313.
   Google Scholar
• Mukaiyama, T. Explorations into new reaction chemistry. Angew. Chem., Int. Ed. 2004, 43, 5590.
   Google Scholar
• Garegg, P.J. Thioglycosides as glycosyl donors in oligosaccharide synthesis. Adv. Carbohydr. Chem. Biochem. 1997, 52, 179.
   PubMed Web of Science ®Google Scholar
• Oscarson, S.Thioglycosides. In Carbohydrates in Chemistry and Biology, Wiley-VCH Verlag GmbH: Weinheim, 2000; pp 93.
   Google Scholar
• Lopez, J.C.; Uriel, C.; Guillamon-Martin, A.; Valverde, S.; Gomez, A.M. IPy2BF4-mediated transformation of n-pentenyl glycosides to glycosyl fluorides: A new pair of semiorthogonal glycosyl donors. Org. Lett. 2007, 9, 2759.
   PubMed Web of Science ®Google Scholar
• Fraser-Reid, B.; Madsen, R. Oligosaccharide synthesis by n-pentenyl glycosides. In Preparative Carbohydrate Chemistry, Dekker: New York, 1997; pp 339.
   Google Scholar
• Fraser-Reid, B.; Anilkumar, G.; Gilbert, M.R.; Joshi, S.; Kraehmer, R. Glycosylation methods: Use of n-pentenyl glycosides. In Carbohydrates in Chemistry and Biology, Wiley-VCH Verlag GmbH: Weinheim, 2000; pp 135.
   Google Scholar
• Williams, L.J.; Garbaccio, R.M.; Danishefsky, S.J. Iterative assembly of glycals and glycal derivatives: The synthesis of glycosylated natural products and complex oligosaccharides. In Carbohydrates in Chemistry and Biology, Wiley-VCH Verlag GmbH: Weinheim, 2000; pp 61.
   Google Scholar
• Kiso, M.; Anderson, L. Protected glycosides and disaccharides of 2-amino-2-deoxy-D-glucopyranose by ferric chloride-catalyzed coupling. Carbohydr. Res. 1985, 136, 309.
   PubMed Web of Science ®Google Scholar
• Marra, A.; Gauffeny, F.; Sinay, P. A novel class of glycosyl donors: Anomeric S-xanthates of 2-azido-2-deoxy-D-galactopyranosyl derivatives. Tetrahedron 1991, 47, 5149.
   Web of Science ®Google Scholar
• Chenault, H.K.; Castro, A. Glycosyl transfer by isopropenyl glycosides: Trisaccharide synthesis in one pot by selective coupling of isopropenyl and n-pentenyl glycopyranosides. Tetrahedron Lett. 1994, 35, 9145.
   Web of Science ®Google Scholar
• Stick, R.V.; Tilbrook, D.M. G.; Williams, S.J. The selective activation of telluro- over seleno-β-D-glucopyranosides as glycosyl donors: A reactivity scale for various telluro, seleno and thio sugars. Aust. J. Chem. 1997, 50, 237.
   Web of Science ®Google Scholar
• Takeuchi, K.; Tamura, T.; Mukaiyama, T. The trityl tetrakis(pentafluorophenyl)borate catalyzed stereoselective glycosylation using new glycosyl donor, 3,4,6-tri-O-benzyl-2-O-p-toluoyl-β-D-glucopyranosyl phenylcarbonate. Chem. Lett. 2000, 122.
   Web of Science ®Google Scholar
• Bogusiak, J.; Szeja, W. Block synthesis of oligosaccharides. Part 1: Preparation of furanosyl-1-thiopyranosides. Tetrahedron Lett. 2001, 42, 2221.
   Web of Science ®Google Scholar
• Huang, X.; Huang, L.; Wang, H.; Ye, X.-S. Iterative one-pot synthesis of oligosaccharides. Angew. Chem. Int. Ed. 2004, 43, 5221.
   PubMed Web of Science ®Google Scholar
• Romero, J.A. C.; Tabacco, S.A.; Woerpel, K.A. Stereochemical reversal of nucleophilic substitution reactions depending upon substituent: Reactions of heteroatom-substituted six-membered-ring oxocarbenium ions through pseudoaxial conformers. J. Am. Chem. Soc. 1999, 122, 168.
   Web of Science ®Google Scholar
• Nicolaou, K.C.; Dolle, R.E.; Papahatjis, D.P. Practical synthesis of oligosaccharides. Partial synthesis of avermectin B1a. J. Am. Chem. Soc. 1984, 106, 4189.
   Web of Science ®Google Scholar
• Halcomb, R.L.; Danishefsky, S.J. On the direct epoxidation of glycals: Application of a reiterative strategy for the synthesis of β-linked oligosaccharides. J. Am. Chem. Soc. 1989, 111, 6661.
   Web of Science ®Google Scholar
• Friesen, R.W.; Danishefsky, S.J. On the controlled oxidative coupling of glycals: A new strategy for the rapid assembly of oligosaccharides. J. Am. Chem. Soc. 1989, 111, 6656.
   Web of Science ®Google Scholar
• Codée, J.D. C.; Litjens, R.E. J. N.; van den Bos, L.J.; Overkleeft, H.S.; van der Marel, G.A. Thioglycosides in sequential glycosylation strategies. Chem. Soc. Rev. 2005, 34, 769.
   PubMed Web of Science ®Google Scholar
• Gin, D. Dehydrative glycosylation with 1-hydroxy donors. J. Carbohydr. Chem. 2002, 21, 645.
   Web of Science ®Google Scholar
• Crich, D.; Cai, W. Chemistry of 4,6-O-benzylidene-d-glycopyranosyl triflates: Contrasting behavior between the gluco and manno series. J. Org. Chem. 1999, 64, 4926.
   PubMed Web of Science ®Google Scholar
• Crich, D.; Sun, S. Direct chemical synthesis of β-mannopyranosides and other glycosides via glycosyl triflates. Tetrahedron 1998, 54, 8321.
   Web of Science ®Google Scholar
• Heuckendorff, M.; Bendix, J.; Pedersen, C.M.; Bols, M. β-Selective mannosylation with a 4,6-silylene-tethered thiomannosyl donor. Org. Lett. 2014, 16, 1116.
   PubMed Web of Science ®Google Scholar
• Kim, J.-H.; Yang, H.; Park, J.; Boons, G.-J. A general strategy for stereoselective glycosylations. J. Am. Chem. Soc. 2005, 1272090.
   Google Scholar
• Ranade, S.C.; Demchenko, A.V. Mechanism of chemical glycosylation: Focus on the mode of activation and departure of anomeric leaving groups. J. Carbohydr. Chem. 2013, 32, 1.
   Web of Science ®Google Scholar
• Yan, L.; Kahne, D. Generalizing glycosylation: Synthesis of the blood group antigens Lea, Leb, and Lex using a standard set of reaction conditions. J. Am. Chem. Soc. 1996, 118, 9239.
   Web of Science ®Google Scholar
• Nukada, T.; Bérces, A.; Whitfield, D.M. Can the stereochemical outcome of glycosylation reactions be controlled by the conformational preferences of the glycosyl donor? Carbohydr. Res. 2002, 337, 765.
   PubMed Web of Science ®Google Scholar
• Whitfield, D.M.; Douglas, S.P.; Tang, T.-H.; Csizmadia, I.G.; Pang, H.Y. S.; Moolten, F.L.; Krepinsky, J.J. Differential reactivity of carbohydrate hydroxyls in glycosylations. II. The likely role of intramolecular hydrogen bonding on glycosylation reactions. Galactosylation of nucleoside 5′-hydroxyls for the syntheses of novel potential anticancer agents. Can. J. Chem 1994, 72, 2225.
   Web of Science ®Google Scholar
• Dasgupta, F.; Garegg, P.J. Alkyl sulfenyl triflate as activator in the thioglycoside-mediated formation of β-glycosidic linkages during oligosaccharide synthesis. Carbohydr. Res. 1988, 177, c13.
   Google Scholar
• Martichonok, V.; Whitesides, G.M. Stereoselective α-sialylation with sialyl xanthate and phenylsulfenyl triflate as a promotor. J. Org. Chem. 1996, 61, 1702.
   PubMed Web of Science ®Google Scholar
• Crich, D.; Sun, S. Direct formation of β-mannopyranosides and other hindered glycosides from thioglycosides. J. Am. Chem. Soc. 1998, 120, 435.
   Web of Science ®Google Scholar
• Lu, X.; Kamat, M.N.; Huang, L.; Huang, X. Chemical synthesis of a hyaluronic acid decasaccharide. J. Org. Chem. 2009, 74, 7608.
   PubMed Web of Science ®Google Scholar
• Dinkelaar, J.; Gold, H.; Overkleeft, H.S.; Codée, J.D. C.A.; van der Marel, G.A. Synthesis of hyaluronic acid oligomers using chemoselective and one-pot strategies. J. Org. Chem. 2009, 74, 4208.
   PubMed Web of Science ®Google Scholar
• Blatter, G.; Jacquinet, J.-C. The use of 2-deoxy-2-trichloroacetamido-D-glucopyranose derivatives in syntheses of hyaluronic acid-related tetra-, hexa-, and octa-saccharides having a methyl β-D-glucopyranosiduronic acid at the reducing end. Carbohydr. Res. 1996, 288, 109.
   PubMed Web of Science ®Google Scholar
• Sun, B.; Srinivasan, B.; Huang, X. Pre-activation-based one-pot synthesis of an α-(2,3)-sialylated core-fucosylated complex type bi-antennary N-glycan dodecasaccharide. Chem. – Eur. J. 2008, 14, 7072.
   PubMed Web of Science ®Google Scholar
• Gao, J.; Guo, Z. Synthesis of a tristearoyl lipomannan via preactivation-based iterative one-pot glycosylation. J. Org. Chem. 2013, 78, 12717.
   PubMed Web of Science ®Google Scholar
• Nokami, T.; Hayashi, R.; Saigusa, Y.; Shimizu, A.; Liu, C.-Y.; Mong, K.-K. T.; Yoshida, J.-i. Automated solution-phase synthesis of oligosaccharides via iterative electrochemical assembly of thioglycosides. Org. Lett. 2013, 15, 4520.
   PubMed Web of Science ®Google Scholar
• Seeberger, P.H. Automated carbohydrate synthesis as platform to address fundamental aspects of glycobiology—Current status and future challenges. Carbohydr. Res. 2008, 343, 1889.
   PubMed Web of Science ®Google Scholar
• Peng, P.; Xiong, D.-C.; Ye, X.-S. Ortho-Methylphenylthioglycosides as glycosyl building blocks for preactivation-based oligosaccharide synthesis. Carbohydr. Res. 2014, 384, 1.
   PubMed Web of Science ®Google Scholar