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Synthesis 2014; 46(07): 923-932
DOI: 10.1055/s-0033-1340617
DOI: 10.1055/s-0033-1340617
paper
Synthesis of C2-Methylene Glycitols from 1,2-Cyclopropanated Sugars: En Route to Iminosugar Analogues
Further Information
Publication History
Received: 05 November 2013
Accepted after revision: 19 December 2013
Publication Date:
30 January 2014 (online)
Abstract
C2-Methylene glycitols were synthesized in three steps by halonium ion mediated solvolytic ring opening of 1,2-cyclopropanated sugars, dehydrohalogenation using potassium carbonate in aqueous acetonitrile, and reduction with sodium borohydride. The generality of the methodology was evaluated by applying it to a series of 1,2-cyclopropanated pyranoses as well as furanoses to give the corresponding C2-methylene glycitol derivatives. Furthermore, the obtained glycitols were converted into 1-deoxy-C2-methylene iminosugar derivatives.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
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