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Carbohydr Res. 2013 Mar 7;368:35-9. doi: 10.1016/j.carres.2012.11.008. Epub 2012 Nov 21.

Concise synthesis of α-galactosyl ceramide from D-galactosyl iodide and D-lyxose.

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  • 1Department of Chemistry, National Chung Hsing University, Taichung 402, Taiwan.

Abstract

α-Galactosyl ceramide is synthesized from d-lyxose in 32% overall yield in five steps. The short and efficient protocol involves a one-pot protection and glycosidation of D-lyxose with D-galactosyl iodide as a key step. The α-linked disaccharide obtained was subsequently transformed into α-galactosyl ceramide in four steps involving Z-selective Wittig olefination at C-1, stereo-inversion at C-4 using azide, one-pot reduction of azide and amidation, and global deprotection.

Copyright © 2012 Elsevier Ltd. All rights reserved.

PMID:
23333444
[PubMed - indexed for MEDLINE]
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