Expeditious Synthesis of Mycobacterium tuberculosis Sulfolipids SL-1 and Ac2SGL Analogues

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• 作者：Vikram A. Sarpe ; Suvarn S. Kulkarni
• 刊名：Organic Letters
• 出版年：2014
• 出版时间：November 7, 2014
• 年：2014
• 卷：16
• 期：21
• 页码：5732-5735
• 全文大小：369K
• ISSN：1523-7052

文摘

M. tuberculosis sulfoglycolipids SL-1 and Ac₂SGL are highly immunogenic and potential vaccine candidates. A short and efficient methodology is reported for the synthesis of SL-1 and Ac₂SGL analogues via regioselective functionalization of 伪,伪-d-trehalose employing a highly regioselective late stage sulfation, as a key step. The SL-1 analogues 3a and 4 were obtained in 10 and 9 steps in 13.4% and 23.9% overall yields, respectively. The Ac₂SGL analogue 5 was synthesized in 5 steps in 18.4% yield.