Glycosyl Bunte Salts: A Class of Intermediates for Sugar Chemistry

Org Lett. 2018 Jan 5;20(1):76-79. doi: 10.1021/acs.orglett.7b03400. Epub 2017 Dec 15.

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.

Publication types

  • Research Support, Non-U.S. Gov't