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Direct and Efficient Glycosylation Protocol for Synthesizing α‐Glycolipids: Application to the Synthesis of KRN7000
Author(s) -
Boutureira Omar,
MoralesSerna José Antonio,
Díaz Yolanda,
Matheu M. Isabel,
Castillón Sergio
Publication year - 2008
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200701228
Subject(s) - chemistry , glycosylation , glycolipid , ceramide , yield (engineering) , iodide , stereoselectivity , combinatorial chemistry , stereochemistry , biochemistry , organic chemistry , catalysis , apoptosis , materials science , metallurgy
Herein we describe a simple and practical protocol for accessing the biologically active galactosyl ceramide KRN7000 and other α‐glycolipids with excellent yield and stereoselectivity by using per‐ O ‐silylated galactosyl iodide and stannyl ethers as glycosylation partners. This direct glycosylation reaction reduces the overall number of steps and provides rapid access to biologically important α‐galactosyl ceramide derivatives. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)