A General and Stereoselective Route to - or -Galactosphingolipids via a Common Four-Carbon Building Block

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• 作者：Pamela Matto ; Emilia Modica ; Laura Franchini ; Federica Facciotti ; Lucia Mori ; Gennaro De Libero ; Grazia Lombardi ; Silvia Fallarini ; Luigi Panza ; Federica Compostella ; Fiamma Ronchetti
• 刊名：Journal of Organic Chemistry
• 出版年：2007
• 出版时间：September 28, 2007
• 年：2007
• 卷：72
• 期：20
• 页码：7757 - 7760
• 全文大小：94K
• 年卷期：v.72,no.20(September 28, 2007)
• ISSN：1520-6904

文摘

A general synthetic strategy toward - or -galactosylceramides and their analogues from 3-azido-2-O-benzyl-1-O-(4-methoxybenzyl)butane-1,2,4-triol is described. The key stepsfor the installation of the main lipid chain are either adiasteroselective alkynylation reaction yielding the 4R stereocenter of phytosphingosine or a Wittig olefination generating the trans double bond of sphingosine. The methodology allows the preparation of different glycolipids withvariations in the structure of the sphingoid base. In particular,three -GalCer-related compounds have been synthesizedand evaluated for their ability to activate CD1d-restrictedT-cells.