Laboratory of Organic Chemistry for Drug Development and Medical Research Laboratories, Department of Pharmaceutical Sciences, Kitasato University, Tokyo 108-8641, Japan.
J Org Chem. 2021 Apr 16;86(8):5973-5982. doi: 10.1021/acs.joc.1c00130. Epub 2021 Apr 8.
Boronic acid-catalyzed regioselective Koenigs-Knorr-type glycosylation is presented. The reaction of an unprotected or partially protected glycosyl acceptor with a glycosyl halide donor in the presence of silver oxide and a low catalytic amount of imidazole-containing boronic acid was found to proceed smoothly, which enables construction of a 1,2- glycosidic linkage with high regioselectivities. This is the first example of the use of a boronic acid catalyst to initiate regioselective glycosylation via the activation of -vicinal diols in glycosyl acceptors.
硼酸催化的区域选择性 Koenigs-Knorr 型糖苷化反应。在氧化银和低催化量的含咪唑硼酸的存在下，未保护或部分保护的糖基受体与糖基卤化物供体反应，反应顺利进行，从而能够以高区域选择性构建 1,2-糖苷键。这是首次使用硼酸催化剂通过激活糖基受体中的邻二醇来引发区域选择性糖苷化反应的实例。
