Gram Scale Synthesis of the Glucuronide Metabolite of ABT-724

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• 作者：Kenneth M. Engstrom ; Jerome F. Daanen ; Seble Wagaw ; Andrew O. Stewart
• 刊名：Journal of Organic Chemistry
• 出版年：2006
• 出版时间：October 27, 2006
• 年：2006
• 卷：71
• 期：22
• 页码：8378 - 8383
• 全文大小：115K
• 年卷期：v.71,no.22(October 27, 2006)
• ISSN：1520-6904

文摘

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A gram scale synthesis of the glucuronide metabolite of ABT-724 is reported. Glycosidic coupling betweena trichloroacetimidate glucuronyl donor and a Cbz-protected hydroxypyridylpiperazine glycosyl acceptoris the key step in the synthesis, since attempts to directly glucuronidate the aglycon, aglycon derivatives,and other truncated glycosyl acceptors were unsuccessful. The route was used to produce 2.1 g of metabolitein eight steps from 2-chloro-5-hydroxypyridine in 21% overall yield.