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Glycosyl Bunte Salts: A Class of Intermediates for Sugar Chemistry

Author:
Meguro, Yasuhiro, Noguchi, Masato, Li, Gefei, Shoda, Shin-ichiro
Source:
Organic letters 2018 v.20 no.1 pp. 76-79
ISSN:
1523-7052
Subject:
chemical reactions, chemical structure, organic compounds, sodium, solvents, sugars, thiosulfates
Abstract:
S-Glycosyl thiosulfates have been discovered as a new class of synthetic intermediates in sugar chemistry, named “glycosyl Bunte salts” after 19th-century German chemist, Hans Bunte. The synthesis was achieved by direct condensation of unprotected sugars and sodium thiosulfate using a formamidine-type dehydrating agent in water–acetonitrile mixed solvent. The application of glycosyl Bunte salts is demonstrated with transformation reactions into other glycosyl compounds such as a 1-thio sugar, a glycosyl disulfide, a 1,6-anhydro sugar, and an O-glycoside.
Agid:
6083259