Branched-chain sugars. Part XIV. Reactions of some glycosulose derivatives with diazomethane: ring expansion of glycosulose derivatives
- 1 January 1973
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- p. 632-638
- https://doi.org/10.1039/p19730000632
Abstract
Epoxidation of methyl 4,6-O-benzylidene-2-deoxy-α-D-erythro-hexopyranosid-3-ulose (1) and of 5-O-benzoyl-1,2-O-isopropylidene-α-D-erythro-pentofuranos-3-ulose (12) by treatment with diazomethane in methanol–ether has been shown to be accompanied by ring expansion (methylene insertion). The structures and configurations of the products have been established. Some aspects of the stereochemical course of the reactions are discussed.Keywords
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