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Concise synthesis of alpha-galactosyl ceramide from D-galactosyl iodide and D-lyxose

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Title Concise synthesis of alpha-galactosyl ceramide from D-galactosyl iodide and D-lyxose
 
Creator YEN, YF
KULKARNI, SS
CHANG, CW
LUO, SY
 
Subject alpha-Galactosyl ceramide
KRN7000
Glycosyl iodide
One-pot protection-glycosylation
Wittig reaction
SPONGE AGELAS-MAURITIANUS
ONE-POT PROTECTION
EFFICIENT SYNTHESIS
CELL LIGAND
T-CELLS
KRN7000
GLYCOSYLATION
GLYCOLIPIDS
ACTIVATION
MOLECULES
 
Description alpha-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 alpha-linked disaccharide obtained was subsequently transformed into alpha-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. (C) 2012 Elsevier Ltd. All rights reserved.
 
Publisher ELSEVIER SCI LTD
 
Date 2014-10-14T12:31:11Z
2014-10-14T12:31:11Z
2013
 
Type Article
 
Identifier CARBOHYDRATE RESEARCH, 36835-39
http://dx.doi.org/10.1016/j.carres.2012.11.008
http://dspace.library.iitb.ac.in/jspui/handle/100/14425
 
Language en