Construction of All O -Alkoxy D-Tetrose and D-Pentose Stereoisomers from 2,3- O -Isopropylidene-D-glyceraldehyde Using 2-(Trimethylsilyl)thiazole as a Formyl Anion Equivalent
1992; Thieme Medical Publishers (Germany); Volume: 1992; Issue: 1/2 Linguagem: Inglês
10.1055/s-1992-34170
ISSN1437-210X
AutoresAlessandro Dondoni, J. Orduna, Pedro Merino,
Tópico(s)Chemical Synthesis and Reactions
ResumoAll 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.
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