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Synthesis of a Versatile Building Block for the Preparation of 6-N-Derivatized α-Galactosyl Ceramides: Rapid Access to Biologically Active Glycolipids

Jervis, Peter J. and Cox, Liam R. and Besra, Gurdyal S. (2010) Synthesis of a Versatile Building Block for the Preparation of 6-N-Derivatized α-Galactosyl Ceramides: Rapid Access to Biologically Active Glycolipids. The Journal of Organic Chemistry, 76 (1). pp. 320-323. ISSN 0022-3263

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URL of Published Version: http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3018865/?tool=pubmed

Identification Number/DOI: doi:10.1021/jo102064p

A concise route to the 6-azido-6-deoxy-α-galactosyl-phytosphingosine derivative 9 is reported. Orthogonal protection of the two amino groups allows elaboration of 9 into a range of 6-N-derivatized α-galactosyl ceramides by late-stage introduction of the acyl chain of the ceramide and the 6-N-group in the sugar head-group. Biologically active glycolipids 6 and 8 have been synthesized to illustrate the applicability of the approach.

Type of Work:Article
Date:14 December 2010 (Publication)
School/Faculty:Colleges (2008 onwards) > College of Life & Environmental Sciences
Department:School of Biosciences
Subjects:Q Science (General)
Institution:University of Birmingham
Copyright Holders:ACS
ID Code:542
Refereed:YES
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