Stereochemistry of Nucleophilic Addition Reactions. 10. Preparation of 2-C-Diacetylmethyl and 2-C-Acetylmethyl Derivatives with the Altro, Gluco, and Manno Configuration from Methyl 4,6-O-Benzylidene-2,3-dideoxy-3-nitro-α-d-erythro-hex-2-enopyranoside

Abstract

Abstract Reaction of the title compound with acetylacetone in the presence of a catalytic amount of sodium hydroxide afforded the 2-C-diacetylmethyl and 2-C-acetylmethyl derivatives having the altro, gluco, and manno configurations. The 2-C-diacetylmethyl derivative with the altro configuration exceptionally exists in a skew boat form. The product ratio depends on solvent and the amount of THF.