Photoreaction of methyl and phenyl 4,6-O-benzylidene-2,3-dideoxy-2-C-p-tolylsulfonyl-β-d-erythro-hex-2-enopyranosides in methanol Original Research Article

The title compounds were irradiated with a high-pressure mercury lamp in methanol to give 2-C-hydroxymethyl derivatives having the gluco, altro, and allo configurations as well as an SN2′ product. Equatorial attack of a hydroxymethyl radical slightly predominated over axial attack. During chromatographic separation on a silica gel column, partial migration of the 4,6-O-benzylidene group in the gluco and altro products occurred to yield the 3′,4-O-benzylidene derivatives.