Convenient stereoselective synthesis of substituted ureido glycosides using stable 4-chlorophenylcarbamates without the requirement of lewis acids

van der Wal, S., Fu, O., Rontogianni, S., Pieters, R. and Liskamp, R. M. J. (2014) Convenient stereoselective synthesis of substituted ureido glycosides using stable 4-chlorophenylcarbamates without the requirement of lewis acids. Synlett, 25(02), pp. 205-208. (doi:10.1055/s-0033-1340220)

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Publisher's URL: http://dx.doi.org/10.1055/s-0033-1340220

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.

Item Type:Articles (Letter)
Status:Published
Refereed:Yes
Glasgow Author(s) Enlighten ID:Liskamp, Professor Robert
Authors: van der Wal, S., Fu, O., Rontogianni, S., Pieters, R., and Liskamp, R. M. J.
College/School:College of Science and Engineering > School of Chemistry
Journal Name:Synlett
Publisher:Georg Thieme Verlag
ISSN:0936-5214
ISSN (Online):1437-2096

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