期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 73, 期 22, 页码 9192-9195出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo8019994
关键词
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资金
- University of Piemonte Orientale, Vercelli (Italy)
- Interdisciplinary Research Center of Autoimmune Diseases (IRCAD) Novara (Italy)
- Compagnia di San Paolo, Torino (Italy)
- Novartis Vaccines, Siena (Italy)
- Regione Piemonte [4/2006]
A new practical synthesis of alpha-GalCer and of its analogues is presented, opening the chance to easily modify the sphingosine chain. The common precursor is a disaccharide, obtained by coupling tetra-O-benzyl-D-galactose with allyl 2,3-O-isopropylidene-D-lyxofuranoside. Introduction of alkyl chains via Wittig reaction (for alpha-GalCer and OCH) or via Williamson reaction (for oxa analogues) followed by standard synthetic steps allows one to efficiently obtain such compounds. The analogues are able to activate iNKT cells when presented by CD1d expressing cells.
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