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

A novel promising strategy for the transformation of nitrosugars into branched pyrrolidines, based on double Henry reaction with formaldehyde followed by reductive ring closure, allowed the first enantiospecific synthesis of a 4-C-hydroxymethyl branched derivative of the well-known glycosidase inhibitor 1,4-dideoxy-1,4-imino-pentanol. This strategy also afforded a new route to some other interesting derivatives, such as N-hydroxy, N-propyloxy, and imino derivatives, a new kind of compounds with promising biological properties.一种基于与甲醛的双亨利反应（double Henry reaction）后经还原环合步骤（reductive ring closure），将亚硝基糖（nitrosugars）转化为支链吡咯烷（branched pyrrolidines）的新颖且极具应用前景的策略，首次完成了经典糖苷酶抑制剂（glycosidase inhibitor）1,4-二脱氧-1,4-亚氨基戊醇的4-C-羟甲基支链衍生物的对映特异性合成。该策略同时为一系列其他具有研究价值的衍生物提供了全新合成路径，包括N-羟基、N-丙氧基及亚氨基类衍生物——这类全新化合物均展现出极具潜力的生物活性。