Iodine-sodium cyanoborohydride-mediated reductive ring opening of 4,6-O-benzylidene acetals of hexopyranosides

A quick efficient and convenient method for the regiospecific reductive ring opening of 4 6-O-benzylidene acetals of O-/S-alkyl/aryl glycosides of mono- and disaccharides leading to the exclusive formation of the corresponding 6-O-benzyl ethers using sodium cyanoborohydride in the presence of molecular iodine is reported It has been observed that common protecting groups such as ethers and esters are well tolerated under the conditions studied The reaction was proved unsuccessful when applied to a glucosamine-derived benzylidene acetal (C) 2010 Elsevier Ltd All rights reserved