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Synthesis 1992; 1992(1/2): 201-210
DOI: 10.1055/s-1992-34170
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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

Alessandro Dondoni* , Jesus Orduna, Pedro Merino
  • *Dipartimento di Chimica, Laboratorio di Chimica Organica, Università Ferrara, Italy
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Publication Date:
18 September 2002 (online)

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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.

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