Synthesis and conformational analysis of substituted 2,6-dioxabicycloheptanes: 1,3-anhydro-2,4-di-O-benzyl-6-deoxy-β-D-glucopyranose by 1H-NMR spectroscopy and molecular mechanics calculation

Article abstract of DOI:10.1016/S0008-6215(00)90481-6

A highly selective ring opening reduction of methyl 3-O-allyl-2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside provided the 2,4-di-O-benzyl derivative.This was toluenesulfonylated or iodinated and subsequently reduced to give crystalline methyl 3-O-allyl-