REACTIONS OF β-d-HEXOPYRANOSIDE INVOLVING α-NITROOLEFIN STRUCTURE WITH SOME S-YLIDES
- 5 December 1972
- journal article
- Published by Oxford University Press (OUP) in Chemistry Letters
- Vol. 1 (12) , 1219-1222
- https://doi.org/10.1246/cl.1972.1219
Abstract
Treatment of methyl 4,6-O-benzylidene-2,3-dideoxy-3-nitro-β-d-erythro-hex-2-enopyranoside (1) with dimethylsulfoxonium methylide and dimethylsulfuranylidene acetophenone afforded the corresponding cyclopropane derivative 3 (75%) and 4 (71%), respectively. In the case of ethyl (dimethylsulfuranylidene) acetate, however, stable ylide (6) which involves two isomers was obtained in 75% yield. Catalytic reduction of 6 gave quantitatively ethoxycarbonylmethyl derivative (7) which has gluco-configuration.This publication has 4 references indexed in Scilit:
- Alkaline Epoxidation of Carbohydrate NitroolefinsCanadian Journal of Chemistry, 1971
- Preparation of Methyl 2,3-Anhydro-4,6-O-benzylidene-3-deoxy-3-nitro-β-d-allopyranoside and Some C2-Branched-Chain Derivatives of Methyl 4,6-O-Benzylidene-2,3-dideoxy-3-nitro-β-d-glucopyranosideBulletin of the Chemical Society of Japan, 1970
- Reactions of Conjugated Nitro Olefins with Phosphoranes and with Dimethylsulfoxonium Methylide to Give Ylides and Nitrocyclopropanes, RespectivelyThe Journal of Organic Chemistry, 1968
- Cyclopropanes from reactions of ethyl dimethylsulfuranylideneacetate with .alpha.,.beta.-unsaturated compoundsThe Journal of Organic Chemistry, 1967