Synthesis 2014; 46(07): 923-932
DOI: 10.1055/s-0033-1340617
paper
© Georg Thieme Verlag Stuttgart · New York

Synthesis of C2-Methylene Glycitols from 1,2-Cyclopropanated Sugars: En Route to Iminosugar Analogues

Kalapati Seshadri
School of Chemistry, University of Hyderabad, Hyderabad 500 046, India   Fax: +91(40)23012460   Email: p_ramu_sridhar@uohyd.ac.in
,
Perali Ramu Sridhar*
School of Chemistry, University of Hyderabad, Hyderabad 500 046, India   Fax: +91(40)23012460   Email: p_ramu_sridhar@uohyd.ac.in
› Author Affiliations
Further Information

Publication History

Received: 05 November 2013

Accepted after revision: 19 December 2013

Publication Date:
30 January 2014 (eFirst)

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

 
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