Some routes to C2-alkoxymethyl hex-2-enopyranosides

Abstract

Several procedures for installing a C2 alkoxy group at C2 of a hex-2-enopyranoside have been investigated. The one that is most convenient for large-scale preparation begins with a 2-keto pyranoside, which is converted into the corresponding exo methylene derivative. An SN2′ rearrangement is effected with thionyl chloride, and the resulting primary allylic chloride is displaced with sodium benzylate.