Dehydrative Glycosylation Using Heptabenzyl Derivatives of Glucobioses and Lactose

Autor:	Masato Okamoto, M. Yamazaki, Yoko Mori, Sonoe Suzuki, Shinkiti Koto, Keiko Kudo, Motoko Hirooka, Hidehiro Kawasaki, T. Irisawa, Shonosuke Zen, Yasushi Takahashi, Koichi Shimizu, Naohiko Morishima, Takashi Higuchi, Y. Hashimoto, Hisamitsu Haigoh, Takako Ikegaki, Sonoko Shichi
Rok vydání:	1992
Předmět:	chemistry.chemical_classification Anomer Disaccharide General Chemistry Medicinal chemistry Chloride chemistry.chemical_compound chemistry Aldose medicine Moiety Silver trifluoromethanesulfonate Trisaccharide Triethylamine medicine.drug
Zdroj:	Bulletin of the Chemical Society of Japan. 65:3257-3274
ISSN:	1348-0634 0009-2673
DOI:	10.1246/bcsj.65.3257
Popis:	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.
Databáze:	OpenAIRE
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