The Direct Synthesis of Methyl 2,4-Di-O-benzyl-α-D-xylopyranoside by the Regiospecific Benzylation of Methyl α-D-Xylopyranoside

Article abstract of DOI:10.1246/bcsj.55.631

The regiospecific benzylation of methyl α-D-xylopyranoside with benzyl chloride and sodium hydride produces methyl 2,4-di-O-benzyl-α-D-xylopyranoside in a 70percent yield, together with the by-products, methyl 2,3- and 3,4-di-O-benzyl-α-D-xylopyranosides.The structure of the 2,4-di-O-benzyl derivative was confirmed through the alternative synthesis of the 2,3- and 3,4-di-O-benzyl derivatives via the O-isopropylidene and O-cyclohexylidene derivatives of methyl α-D-xylopyranoside.