Single‐Step Multisyntheses of Glycosyl Acceptors: Benzylation of n‐1 Hydroxyl Groups of Phenylthio Glycosides of Xylose, Mannose, Glucose, Galactose, 2‐Azido‐2‐deoxy‐glucose, and 2‐Azido‐2‐deoxy‐galactose

References

• Pouncey , L. , Easton , J. , Heath , L. S. , Grenet , J. and Kidd , V. J. 1991 . Beta 1‐4‐galactosyltransferase gene expression is regulated during entry into the cell cycle and during the cell cycle . Somat. Cell Molec. Genet. , 17 ( 5 ) : 435 – 443 .
   Google Scholar
• Ladisch , S. , Becker , H. and Ulsh , L. 1992 . Immunosuppression by human gangliosides: I. Relationship of carbohydrate structure to the inhibition of T cell responses . Biochem. Biophys. Acta , 1125 ( 2 ) : 180 – 188 .
   PubMed Web of Science ®Google Scholar
• Miller , D. J. and Ax , R. L. 1990 . Carbohydrates and fertilization in animals . Mol. Reprod. Dev. , 26 ( 2 ) : 184 – 198 .
   Google Scholar
• Karlsson , K.‐A. 1989 . Animal glycosphingolipids as membrane attachment sites for bacteria . Annu. Rev. Biochem. , 58 : 309 – 350 .
   PubMed Web of Science ®Google Scholar
• Suzuki , Y. 1994 . Gangliosides as influenza virus receptors. Variation of influenza viruses and their recognition of the receptor sialo‐sugar chains . Prog. Lipid Res. , 33 : 429 – 457 .
   PubMed Web of Science ®Google Scholar
• Braccini , I. , Derouet , C. , Esnault , J. , Hervé du Penhoat , C. , Mallet , J.‐M. , Michon , V. and Sinaÿ , P. 1993 . Conformational analysis of nitrilium intermediates in glycosylation reactions . Carbohydr. Res. , 246 : 23 – 41 . and references cited therein
   Web of Science ®Google Scholar
• Lemieux , R. U. 1964 . “ Rearrangements and isomerizations in carbohydrate chemistry ” . In Molecular Rearrangements Edited by: de Mayo , P. 709 – 769 . New York : Interscience .
   Google Scholar
• Kanemitsu , T. , Wong , C.‐H. and Kanie , O. 2002 . Solid‐phase synthesis of oligosacharide and on‐resin quantitative monitoring using gated decoupling 13C‐NMR . J. Am. Chem. Soc. , 124 : 3591 – 3599 .
   PubMed Web of Science ®Google Scholar
• Koto , S. , Uchida , T. and Zen , S. 1973 . Synthesis of isomaltose, isomaltotetraose, and isomaltooctaose . Bull. Chem. Soc. Jpn. , 46 ( 8 ) : 2520 – 2523 .
   Google Scholar
• Nicolaou , K. C. , Dolle , R. E. , Papahatjis , D. P. and Randall , J. L. 1984 . Practical synthesis of oligosaccharides. Partial synthesis of avermectin B1a . J. Am. Chem. Soc. , 106 ( 15 ) : 4189 – 4192 .
   Google Scholar
• Lönn , H. 1985 . Synthesis of a tri‐ and a hepta‐saccharide which contain α‐L‐fucopyranosyl groups and are part of the complex type of carbohydrate moiety of glycoproteins . Carbohydr. Res. , 139 : 105 – 113 .
   PubMed Web of Science ®Google Scholar
• Raghavan , S. and Kahne , D. 1993 . A one‐step synthesis of the ciclamycin trisaccharide . J. Am. Chem. Soc. , 115 : 1580 – 1581 .
   Web of Science ®Google Scholar
• Roy , R. , Andersson , F. O. and Letellier , M. 1992 . Active and latent thioglycosyl donors in oligosaccharide synthesis. Application to the synthesis of α‐sialosides . Tetrahedron Lett. , 33 ( 41 ) : 6053 – 6056 .
   Google Scholar
• Yamada , H. , Harada , T. , Miyazaki , H. and Takahashi , T. 1994 . One‐pot sequential glycosylation: a new method for the synthesis of oligosaccharides . Tetrahedron Lett. , 35 ( 23 ) : 3979 – 3982 .
   Google Scholar
• Kanemitsu , T. , Kanie , O. and Wong , C.‐H. 1998 . Quantitative monitoring of solid‐phase synthesis using gated decoupling 13C NMR spectroscopy with a C‐13‐enriched protecting group and an internal standard in the synthesis of sialyl lewis X tetrasaccharide . Angew. Chem. Int. Eds. , 37 ( 24 ) : 3415 – 3418 .
   Google Scholar
• Kanie , O. , Ito , Y. and Ogawa , T. 1994 . Orthogonal glycosylation strategy in oligosaccharide synthesis . J. Am. Chem. Soc. , 116 ( 26 ) : 12073 – 12074 .
   Google Scholar
• Kanie , O. , Ito , Y. and Ogawa , T. 1996 . Orthogonal glycosylation strategy in synthesis of extended blood group B determinant . Tetrahedron Lett. , 37 ( 26 ) : 4551 – 4554 .
   Google Scholar
• Ito , Y. , Kanie , O. and Ogawa , T. 1996 . Orthogonal glycosylation strategy for rapid assembly of oligosaccharide on polymer support . Angew. Chem. Int. Ed. Engl. , 35 ( 21 ) : 2510 – 2512 .
   Google Scholar
• Garegg , P. J. , Iversen , T. and Oscarson , S. 1976 . Monobenzylation of diols using phase‐transfer catalysis . Carbohydr. Res. , 50 ( 2 ) : C12 – C14 .
   Google Scholar
• Flowers , H. M. 1975 . Selective benzylation of some D‐galactopyranosides. Unusual relative reactivity of the hydroxyl group at C‐4 . Cardohydr. Res. , 39 ( 2 ) : 245 – 251 .
   Google Scholar
• Kanie , O. , Barresi , F. , Ding , Y. , Labbe , J. , Otter , A. , Forsberg , L. S. , Ernst , B. and Hindsgaul , O. 1995 . A strategy of random glycosylation for the production of oligosaccharide libraries . Angew. Chem. Int. Ed. Engl. , 34 ( 23/24 ) : 2720 – 2722 .
   Google Scholar
• Kiso , M. , Ishida , H. and Ito , H. 2000 . “ Special probrems in glycosylation reactions: sialidations ” . In Carbohydrates in Chemistry and Biology Edited by: Ernst , B. , Hart , G. W. and Sinaÿ , P. Vol. 1 , 345 – 365 . Weinheim : Wiley‐VCH .
   Google Scholar
• Haines , A. H. 1976 . Relative reactivities of hydroxyl groups in carbohydrates . Adv. Carbohydr. Chem. Biochem. , 33 : 11 – 109 .
   Google Scholar
• Martin‐Lomas , M. , Flores‐Mosquera , M. and Chiara , J. L. 2000 . Attempted synthesis of type‐A inositolphosphoglycan mediators—synthesis of a pseudohexasaccharide precursor . Eur. J. Org. Chem. , : 1547 – 1562 .
   Google Scholar
• Takahashi , S. , Kuzuhara , H. and Nakajima , M. 2001 . Design and synthesis of a heparanse inhibitor with pseudodisaccharide structure . Tetrahedron , 57 ( 32 ) : 6915 – 6926 .
   Google Scholar
• Pozsgay , V. 1998 . Synthesis of glycoconjugate vaccines against Shigella dysenteriae type 1 . J. Org. Chem. , 63 ( 17 ) : 5983 – 5999 .
   Google Scholar
• Greenberg , W. A. , Priestley , E. S. , Sears , P. S. , Alper , P. B. , Rosenbohm , C. , Hendrix , M. , Hung , S.‐C. and Wong , C.‐H. 1999 . Design and synthesis of new aminoglycoside antibiotics containing neamine as an optimal core structure: correlation of antibiotic activity with in vitro inhibition of translation . J. Am. Chem. Soc. , 121 ( 28 ) : 6527 – 6541 .
   Google Scholar
• Magaud , D. , Grandjean , C. , Doutheau , A. , Anker , D. , Shevchik , V. , Cotte‐Pattat , N. and Robert‐Baudouy , J. 1998 . Synthesis of the two monomethyl esters of the disaccharide 4‐O‐α‐D‐galacturonosyl‐D‐galacturonic acid and of precursors for the preparation of higher oligomers methyl uronated in definite sequences . Carbohydr. Res. , 314 ( 3–4 ) : 189 – 199 .
   Google Scholar
• Ennis , S. C. , Cumpstey , I. , Fairbanks , A. J. , Butters , T. D. , Mackeen , M. and Wormald , M. R. 2002 . Total synthesis of the Glc3Man N‐glycan tetrasaccharide . Tetrahedron , 58 ( 46 ) : 9403 – 9411 .
   Google Scholar
• Motawia , M. S. , Olsen , C. E. , Enevoldsen , K. , Marcussen , J. and Moller , B. L. 1995 . Chemical synthesis of 6′‐α‐maltosyl‐maltotriose, a branched oligosaccharide representing the branch point of starch . Carbohydr. Res. , 277 ( 1 ) : 109 – 123 .
   PubMed Web of Science ®Google Scholar
• Pfaffli , P. J. , Hixson , S. H. and Anderson , L. 1972 . Thioglycosides having O‐benzyl blocking groups as intermediates for the systematic, sequential synthesis of oligosaccharides. Synthesis of isomaltose . Carbohydr. Res. , 23 ( 2 ) : 195 – 206 .
   Google Scholar
• Marzabadi , C. H. and Spilling , C. D. 1993 . Stereoselective glucal epoxide formation . J. Org. Chem. , 58 ( 14 ) : 3761 – 3766 .
   Google Scholar
• Oshitari , T. , Shibasaki , M. , Yoshizawa , T. , Tomita , M. , Takao , K.‐I. and Kobayashi , S. 1997 . Synthesis of 2‐O‐(3‐O‐carbamoyl‐α‐D‐mannopyranosyl)‐L‐gulopyranose: sugar moiety of antitumor antibiotic bleomycin . Tetrahedron , 53 ( 32 ) : 10993 – 11006 .
   Google Scholar
• Lemanski , G. and Ziegler , T. 2000 . Intramolecular mannosylations of glucose derivatives via prearranged glycosides . Helvetica Chim. Acta , 83 ( 10 ) : 2655 – 2675 .
   Google Scholar
• Lemanski , G. and Ziegler , T. 2000 . Synthesis of 4‐O‐D‐mannopyranosyl‐α‐D‐glucopyranosides by intramolecular glycosylation of 6‐O‐tethered mannosyl donors . Tetrahedron , 56 ( 4 ) : 563 – 579 .
   Google Scholar