Construction of AllO-Alkoxy D-Tetrose and D-Pentose Stereoisomers from 2,3-O-Isopropylidene-D-glyceraldehyde Using 2-(Trimethylsilyl)thiazole as a Formyl Anion Equivalent
- 1 January 1992
- journal article
- research article
- Published by Georg Thieme Verlag KG in Synthesis
- Vol. 1992 (1/2) , 201-210
- https://doi.org/10.1055/s-1992-34170
Abstract
All D-tetroses and D-pentoses having differentially protected hydroxy groups are synthesized by an iterative one-carbon chain-elongation cycle commencing with the addition of 2-(trimethylsilyl)thiazole to 2,3-O-isopropylidene-D-glyceraldehyde. One half of the resulting secondary alcohol is epimerized by an oxidation-reduction sequence. The aldehydes are revealed from the two diastereomeric alcohols by thiazole-to-formyl conversion.Keywords
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