Department of Chemistry, Indian Institute of Technology Bombay, Mumbai 400076, India.
J Org Chem. 2011 Aug 19;76(16):6866-70. doi: 10.1021/jo200979n. Epub 2011 Jul 21.
The first synthesis of maradolipid, a unique dissymmetrically 6,6'-di-O-acylated trehalose glycolipid isolated from C. elegans, is accomplished in five steps starting from trehalose in 45% overall yield. The short synthesis relies on dissymmetrization of trehalose core via regioselective acylation of a 2,3,4,2',3',4'-hexa-O-TMS trehalose 6,6'-diol derivative as a key step.
从秀丽隐杆线虫中分离得到的独特不对称 6,6'-二-O-酰基海藻糖糖脂——马拉迪脂的首次全合成,是从海藻糖出发经五步反应以 45%的总收率完成。该合成路线的关键步骤是通过 2,3,4,2',3',4'-六-O-三甲基硅基海藻糖 6,6'-二醇衍生物的区域选择性酰化反应实现糖核的不对称化,从而实现了短路线合成。