Polymer-Assisted Strategy for Deprotection of Protected Sugars

Significance

An efficient method for the deprotection of protected oligosaccharides based on a polymer-assisted strategy was developed. Thus, treatment of methyl 2,3,4-O-tribenzylglucoside (1) with a prelinker 2 (1.2 equiv) under acidic conditions gave the protected glucoside 3. The subsequent amidation of 3 with an ArgoPore resin-supported amine 4 (3.0 equiv) afforded the solid-supported protected glucose 5 in 99% in two steps. The removal of benzyl ethers by Birch reduction and the subsequent acidic treatment gave the α-methyl glucoside 5 in 91% overall yield from 1. This strategy was applied to the synthesis of dimeric and trimeric Lewis X derivatives (7 and 8).