Solid-phase de novo synthesis of a (+/-)-2-deoxy-glycoside

Abstract

The solid-phase synthesis of methyl 2-deoxy-3-O-benzyl-D,L-arabino-hexopyranoside was achieved in a six-step sequence via a de novo strategy based on the hetero-Diels-Alder reaction of a vinyl ether supported on an azalactone-functionalized polystyrene resin, followed by the functional modification of the heteroadduct and the final release of the methyl glycoside by acidic solvolysis.