Synthesis of a versatile building block for the preparation of 6-N-derivatized α-galactosyl ceramides: rapid access to biologically active glycolipids.

Peter Jervis, Liam Cox, Gurdyal Besra

Research output: Contribution to journalArticlepeer-review

29 Citations (Scopus)
165 Downloads (Pure)

Abstract

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.
Original languageEnglish
Pages (from-to)320-3
Number of pages4
JournalThe Journal of Organic Chemistry
Volume76
Issue number1
DOIs
Publication statusPublished - 7 Jan 2011

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