Preliminary Studies on the Transformation of Nitrosugars into Branched Chain Iminosugars: Synthesis of 1,4-Dideoxy-4-C-hydroxymethyl- 1,4-imino-pentanols

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• 作者：José ; M. Otero ; Raquel G. Soengas ; Juan C. Esté ; vez ; Ram&oacute ; n J. Esté ; vez ; David J. Watkin ; Emma L. Evinson ; Robert J. Nash ; George W. J. Fleet
• 刊名：Organic Letters
• 出版年：2007
• 出版时间：February 15, 2007
• 年：2007
• 卷：9
• 期：4
• 页码：623 - 626
• 全文大小：100K
• 年卷期：v.9,no.4(February 15, 2007)
• ISSN：1523-7052

文摘

LE>l062887vn00002>MG SRC="/isubscribe/journals/orlef7/9/i04/figures/ol062887vn00002.gif" ALIGN="left" HSPACE=5>A novel promising strategy for the transformation of nitrosugars into branched pyrrolidines, based on double Henry reaction with formaldehydefollowed by reductive ring closure, allowed the first enantiospecific synthesis of a 4-C-hydroxymethyl branched derivative of the well-knownglycosidase inhibitor 1,4-dideoxy-1,4-imino-pentanol. This strategy also afforded a new route to some other interesting derivatives, such asN-hydroxy, N-propyloxy, and imino derivatives, a new kind of compounds with promising biological properties.