A stereoselective hetero-Diels–Alder approach to Carbon–Carbon linked disaccharides
- 1 January 1994
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Chemical Communications
- No. 17,p. 1963-1964
- https://doi.org/10.1039/c39940001963
Abstract
The chiral 1-oxabuta-1,3-diene 1 bearing the thiazol-2-yl ring at C-2 and the D-galacto-pentopyranosid-5-yl ring at C-4 reacts with ethyl vinyl ether 2 in an endo-specific hetero-Diels–Alder process to give a mixture of diastereoisomeric 3,4-dihydro-2H-pyran derivatives 3 and 4 in 4 : 1 ratio and 97% overall yield; these compounds are transformed by thiazole-to-formyl unmasking and hydroxylation into stereoisomeric C-3–C-5 linked dipyranosides 7 and 8.Keywords
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