Reactions of methyl 4,6-O-benzylidene-2,3-dideoxy-2-C-p-tolylsulfonyl-β-D-erythro-hex-2-en opyranoside and its phenyl analog with several nucleophiles; stereoselective preparation of 3-O-acyl-D-arabino- and D-ribo-hex-1-enitol derivatives

Article abstract of DOI:10.1016/0008-6215(91)80017-H

Reactions of methyl 2-C-p-tolylsulfonyl-2-enopyranoside (6) with nucleophiles (methoxide, nitromethane, 2,4-pentanedione, and ammonia) afforded the β-D-gluco adducts with high stereoselectivity. However, similar treatment of the phenyl analog 11 with sodi