Stereoselective synthesis of (2S,3S,4R,5S)-3,4-dihydroxy-2,5-dihydroxymethyl pyrrolidine from L-sorbose

Sébastien Balieu; Arnaud Guilleret; Romain Reynaud; Agathe Martinez; Arnaud Haudrechy

doi:10.1016/j.carres.2013.03.017

Stereoselective synthesis of (2S,3S,4R,5S)-3,4-dihydroxy-2,5-dihydroxymethyl pyrrolidine from L-sorbose

Carbohydr Res. 2013 Jun 7:374:14-22. doi: 10.1016/j.carres.2013.03.017. Epub 2013 Mar 29.

Authors

Sébastien Balieu¹, Arnaud Guilleret, Romain Reynaud, Agathe Martinez, Arnaud Haudrechy

Affiliation

¹ Institut de Chimie Moléculaire de Reims, UMR CNRS 7312, Université de Reims, Reims, France.

PMID: 23603481
DOI: 10.1016/j.carres.2013.03.017

Abstract

One of the most frequently synthesized iminosugar derivatives is DMDP. Starting from L-sorbose, a practical method for the synthesis of derivatives of this five-membered iminocyclitol has been developed, involving straightforward steps and a convenient selective reduction of a ketoxime intermediate.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Imino Sugars / chemical synthesis*
Imino Sugars / chemistry
Molecular Conformation
Pyrrolidines / chemical synthesis*
Pyrrolidines / chemistry
Sorbose / chemistry*
Stereoisomerism

Substances

Imino Sugars
Pyrrolidines
Sorbose