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Issue 98, 2015
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Divergent de novo synthesis of all eight stereoisomers of 2,3,6-trideoxyhexopyranosides and their oligomers

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Abstract

All eight possible stereoisomers of 2,3,6-trideoxyhexopyranosides are prepared systematically from furan derivatives by a sequence of Achmatowicz rearrangement, Pd-catalysed glycosidation, and chiral catalyst-controlled tandem reductions. This sequence provides access to all possible stereoisomers of naturally occurring rhodinopyranosides, amicetopyranosides, disaccharide narbosine B, and other unnatural oligomeric 2,3,6-trideoxyhexopyranosides. It comprises a unique and systematic strategy for the de novo synthesis of deoxysugars.

Graphical abstract: Divergent de novo synthesis of all eight stereoisomers of 2,3,6-trideoxyhexopyranosides and their oligomers

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Article information


Submitted
17 Sep 2015
Accepted
12 Oct 2015
First published
13 Oct 2015

Chem. Commun., 2015,51, 17475-17478
Article type
Communication

Divergent de novo synthesis of all eight stereoisomers of 2,3,6-trideoxyhexopyranosides and their oligomers

W. Song, Y. Zhao, J. C. Lynch, H. Kim and W. Tang, Chem. Commun., 2015, 51, 17475
DOI: 10.1039/C5CC07787G

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