Crich David, Cai Feng
Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607-7061, USA.
Org Lett. 2007 Apr 12;9(8):1613-5. doi: 10.1021/ol070449y. Epub 2007 Mar 9.
[reaction: see text] The 2-O-[3-(2'-benzyloxyphenyl)-3,3-dimethylpropanoate] and 2-O-[3-(2'-benzyloxy-4',6'-dimethylphenyl)-3,3-dimethylpropanoate] esters enable the synthesis of a range of beta-glucosides and alpha-mannosides through neighboring participation in excellent yield, and are removed by hydrogenolysis in concert with the cleavage of benzyl esters in the presence of other esters making them particularly well suited to the stereocontrolled synthesis of glycosyl esters.
[反应:见正文] 2-O-[3-(2'-苄氧基苯基)-3,3-二甲基丙酸酯]和2-O-[3-(2'-苄氧基-4',6'-二甲基苯基)-3,3-二甲基丙酸酯]酯能够通过邻基参与以优异的产率合成一系列β-葡萄糖苷和α-甘露糖苷,并且在其他酯存在下,通过氢解与苄酯的裂解协同去除,这使得它们特别适合于糖基酯的立体控制合成。