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Synthesis 2017; 49(05): 1087-1092
DOI: 10.1055/s-0036-1588325
DOI: 10.1055/s-0036-1588325
paper
Efficient Synthesis of Orthogonally Protected Rare l-Hexoses and Derivatives
Further Information
Publication History
Received: 01 July 2016
Accepted after revision: 14 September 2016
Publication Date:
13 October 2016 (online)
Abstract
Stereoselective preparations of protected rare sugars and derivatives, namely l-psicose, l-altritol, and l-talose have been achieved in 70, 44, and 18% yield, respectively, from an orthogonally protected l-glyceraldehyde derivative. The key step is the stereoselective proline-catalyzed aldol reaction of this aldehyde with dioxanone.
Key words
organocatalysis - aldol reaction - rare sugars - orthogonal protection - L-psicose - L-talitol - L-altritol - L-taloseSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0036-1588325.
- Supporting Information
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