Unsaturated carbohydrates. Part XVII. Synthesis of branched-chain sugar derivatives by application of the Claisen rearrangement
- 1 January 1973
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- p. 1791-1793
- https://doi.org/10.1039/p19730001791
Abstract
2,3-Dideoxy-4-O-vinylhex-2-enopyranoside derivatives on heating to 180° undergo the Claisen rearrangement to give 2,3,4-trideoxy-2-C-(formylmethyl)hex-3-enopyranoside isomers. Suprafacial [3,3] sigmatropic processes are involved, so that stereochemical integrity is maintained at the allylic centres. The reaction represents a novel means whereby branch points can be introduced into carbohydrates.Keywords
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