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

doi:10.1055/s-1992-34170

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

paper

© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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

Abstract

als PDF herunterladen Alle Artikel dieser Rubrik

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.

PDF (771 kb)