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Dehydrative Glycosylation Using Heptabenzyl Derivatives of Glucobioses and Lactose

1992; Oxford University Press; Volume: 65; Issue: 12 Linguagem: Inglês

10.1246/bcsj.65.3257

1348-0634

Shinkiti Koto, Naohiko Morishima, Sonoko Shichi, Hisamitsu Haigoh, Motoko Hirooka, Mitsuko Okamoto, Takashi Higuchi, Koichi Shimizu, Yosuke Hashimoto, T. IRISAWA, Hidehiro Kawasaki, Yasushi Takahashi, Masayo Yamazaki, Yoko Mori, Keiko Kudo, Takako Ikegaki, Sonoe Suzuki, Shonosuke Zen,

Glycosylation and Glycoproteins Research

Abstract Dehydrative glycosylations of the 2-, 3-, 4-, and 6-OH groups of d-glucopyranose with hepta-O-benzyl derivatives of glucobioses (O-d-glucopyranosyl-(1→n)-d-glucopyranose; n = 2, 3, 4, or 6) and lactose, in the presence of a ternary mixture of p-nitrobenzenesulfonyl chloride, silver trifluoromethanesulfonate, and triethylamine in dichloromethane showed that the selectivity of the reaction depended on the anomeric configuration and the linking position to the reducing tribenzylglucose moiety of the nonreducing tetrabenzylglucosyl residue and on the class of the OH group to be glycosylated. The use of a quaternary mixture of p-nitrobenzenesulfonyl chloride, silver trifluoromethanesulfonate, N,N-dimethylacetamide, and triethylamine made all but the β(1→2)-linked biosyl donor undergo α-condensation. Several new linear trisaccharides were obtained via debenzylation of the condensates.