Stereoselective synthesis of a ketohexofuranose from an aldohexopyranose by a [6+1−1] strategy

Abstract

Ozonolysis of 2-acetoxymethyl-1,5-anhydro-3,4,6-tri- O-benzyl-2-deoxy- D- arabino-hex-1-enitol gave 1- O-acetyl-3,4,6-tri- O-benzyl-4- O-formyl- D- arabino-hex-2-ulose ( 5). Subsequent hydrolysis and acetylation of 5 provided 1,2-di- O-acetyl-3,4,6-tri- O-benzyl- D-fructofuranose 6 in excellent yield. This methodology allows specific deuteration at C-1 of a protected D-fructofuranose derivative. This approach therefore could serve as [6+1−1] formulation for hexose series inter-conversion, that is, aldohexopyranose to ketohexofuranose.