通过迭代二羟基化策略进行C-4-取代糖的从头不对称合成。
De novo asymmetric syntheses of C-4-substituted sugars via an iterative dihydroxylation strategy.
作者信息
Ahmed Md Moinuddin, O'Doherty George A
机构信息
Department of Chemistry, West Virginia University, Morgantown, WV 26506, USA.
出版信息
Carbohydr Res. 2006 Jul 24;341(10):1505-21. doi: 10.1016/j.carres.2006.03.024. Epub 2006 Apr 17.
A short and highly efficient route to various C-4 substituted sugar lactones has been developed. The key to the overall transformation is the sequential osmium-catalyzed dihydroxylation reaction of substituted 2,4-dienoates and an allylic substitution at the C-4 position. When the Sharpless AD-mix procedure is used in a matched sense for the second dihydroxylation reaction, it results in an exceedingly diastereo- and enantioselective synthesis of several C-4-substituted sugars.
已经开发出一条简短且高效的合成各种C-4取代糖内酯的路线。整个转化过程的关键是取代的2,4-二烯酸酯的锇催化顺序二羟基化反应以及C-4位的烯丙基取代反应。当Sharpless不对称双羟基化反应程序以匹配的方式用于第二次二羟基化反应时，可实现几种C-4取代糖的高度非对映和对映选择性合成。
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