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) |
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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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