Alkyloxytris(dimethylamino)phosphonium salts. Part 21. Anomeric hydroxy-group activation of 2,3:4,6-di-O-isopropylidene-α-D-mannopyranose, thioglycosylation and glycosylation
- 1 January 1980
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 2,p. 381-384
- https://doi.org/10.1039/p19800000381
Abstract
The action of carbon tetrachloride and tris(dimethylamino)phosphine at low temperature on 2,3:4,6-di-O-isopropylidene-α-D-mannopyranose affords the α anomeric form of the corresponding alkoxytris(dimethylamino)phosphonium chloride. The condensation of aromatic thiols with this salt leads to β-thiomannosides by an SN2 process and the condensation of alcohols, preceded by the action of silver salts in order to avoid the formation of the glycosyl chlorides, yields a mixture of α- and β-mannosides.This publication has 1 reference indexed in Scilit:
- Mechanisms for the formation of acetylglycosides and orthoesters from acetylglycosyl halidesJournal of Research of the National Bureau of Standards, 1949