Postema M H, Calimente D, Liu L, Behrmann T L
Department of Chemistry, Wayne State University, Detroit, Michigan 48202, USA.
J Org Chem. 2000 Sep 22;65(19):6061-8. doi: 10.1021/jo0005159.
A convergent route to a variety of C-1-disaccharide glycals based on the olefin metathesis reaction of enol ethers and alkenes is described. The DCC-mediated coupling reaction of a variety of pentose enitols (1a-c) with a number of C-5- and C-6-monosaccharide carboxylic acids (2a-e) gave the corresponding esters 3a-l in good yield. Methylenation of these compounds was followed by ring-closing metathesis, mediated by the Schrock molybdenum catalyst 8 in warm toluene, to provide the target C-disaccharide glycals 5a-l. The formed enol ether double bond in 5a was then transformed, via standard manipulations, into a variety of C-disaccharide derivatives 21-25.
描述了一种基于烯醇醚和烯烃的烯烃复分解反应合成多种C-1-二糖缩水甘油醛的汇聚路线。多种戊糖烯醇（1a - c）与多种C-5-和C-6-单糖羧酸（2a - e）在DCC介导下的偶联反应以良好产率得到相应的酯3a - l。这些化合物进行亚甲基化后，在温热的甲苯中由Schrock钼催化剂8介导进行关环复分解反应，得到目标C-二糖缩水甘油醛5a - l。然后通过标准操作将5a中形成的烯醇醚双键转化为多种C-二糖衍生物21 - 25。
