Glycosides. Part 1. New synthesis of 1,2-trans O-aryl glycosides, via tributyltin phenoxides

Abstract

A new method of glycosidation of phenols has been studied. The reaction of tributyltin phenoxides 2 with 1,2,3,4,6-penta-O-acetyl-D-hexopyranosides 3, 7 and 9, in the presence of tin tetrachloride is described. Glycosides 4, 8 and 10 have been isolated in good yields with high 1,2-trans selectivity. The tributyltin phenoxides 2 have been isolated in quantitative yields, starting from phenols 1 and Bu₃SnOMe. This simple method starts from the stable peracetylated sugar, an intermediate of easy access.