Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
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
Tohru SakakibaraAkinori SetaYoshifusa TachimoriRokuro Sudoh
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1980 Volume 53 Issue 8 Pages 2322-2326

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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.

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