Direct and Efficient Glycosylation Protocol for Synthesizing α‐Glycolipids: Application to the Synthesis of KRN7000 | Zendy

Boutureira Omar | Zendy; MoralesSerna José Antonio | Zendy; Díaz Yolanda | Zendy; Matheu M. Isabel | Zendy; Castillón Sergio | Zendy

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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)

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