The Synthesis of Some Alkyl Hex-3-enopyranosiduloses

Abstract

Routes to methyl 3,4-dideoxy-α-D-glycero-hex-3-enopyranosidulose 1a have been developed which use cheap readily-available chemicals, which are operable on a large scale and which have readily crystallizable materials as key intermediates (Scheme 4). Extensive use is made of reductive elimination of vicinal sulfonyloxy groups which is shown to operate equally well whether these groups on the pyranoside ring are in cis or trans relationship. Contrary to other reported cases, it is found that the carbon-2 allylic hydroxyl goup is oxidized with manganese dioxide whether it is in pseudoaxial or equatorial orientation.