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通过 Sonogashira 偶联、不对称环氧化和三氯乙酰亚胺酯介导的环氧化物开环反应合成免疫刺激性的α-C-半乳糖神经酰胺糖脂。

Synthesis of immunostimulatory alpha-C-galactosylceramide glycolipids via Sonogashira coupling, asymmetric epoxidation, and trichloroacetimidate-mediated epoxide opening.

机构信息

Department of Chemistry and Biochemistry, Queens College of The City University of New York, Flushing, New York 11367-1597, USA.

出版信息

Org Lett. 2010 Jul 2;12(13):2974-7. doi: 10.1021/ol1009976.

DOI:10.1021/ol1009976
PMID:20518525
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC2896489/
Abstract

Stereocontrolled syntheses of alpha-C-GalCer (2) and its alpha-C-acetylenic analogue 6 were accomplished in high efficiency by a convergent construction strategy from 1-hexadecene and d-galactose. The key transformations include Sonogashira coupling, Sharpless asymmetric epoxidation, and Et(2)AlCl-catalyzed cyclization of an epoxytrichloroacetimidate to generate protected dihydrooxazine 21.

摘要

通过从 1-十六烯和 D-半乳糖出发的汇聚式构建策略，高效地完成了 α-C-GalCer（2）及其 α-C-炔基类似物 6 的立体选择性合成。关键转化包括 Sonogashira 偶联、Sharpless 不对称环氧化以及 Et(2)AlCl 催化的环氧三氯乙酰亚胺的环化，以生成保护的二氢噁嗪 21。

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