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Synlett 2014; 25(2): 205-208
DOI: 10.1055/s-0033-1340220
DOI: 10.1055/s-0033-1340220
letter
Convenient Stereoselective Synthesis of Substituted Ureido Glycosides Using Stable 4-Chlorophenylcarbamates without the Requirement of Lewis Acids
Further Information
Publication History
Received: 16 September 2013
Accepted after revision: 14 October 2013
Publication Date:
02 December 2013 (online)
Abstract
A modification of the synthesis of substituted ureido glycosides in a stereospecific fashion is described, in which commercially available azido glycosides are reduced to the amines, which are then reacted with 4-chlorophenyl chloroformate to the corresponding 4-chlorophenyl carbamate of the glycosides. These synthetic intermediates are stable at room temperature and have a long shelf life, and can transiently form the 1-isocyanato glycosides under mildly basic conditions, which subsequently can react with amines to form substituted ureido glycosides
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synlett.
- Supporting Information
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