Facile conversion of 2,3,4,6-tetra-O-benzyl-D-glucopyranose into 1,3,4,5-tetra-O-benzyl-L-sorbopyranose
Abstract
The bromomagnesium salts of certain alcohols and phenols in dichloromethane cleanly promote the title transformation; the reaction proceds via formal hydride transfer from C-5 to anomeric carbon of the glucopyranose precursor.