Three different types of organoboron-catalyzed glycosylations using 1,2-O-unprotected sugars have been developed for the synthesis of 1,2-cis-glycosides. Although arylboronic acid-catalyzed dehydrative coupling with glycosyl acceptors provides the thermodynamically controlled products as a mixture of two isomers, diarylborinic acid-catalyzed O-alkylation with O-triflyl sugars gave the desired 1,2-cis-glycosides in a highly stereoselective manner. Furthermore, tricyclic borinate complexes consisted of 1,2-glycosyl diols and diarylborinic acids efficiently promote the O-glycosylation with glycosyl phosphites and anhydrosugars, leading to 1,1′-β,α- and α,α-trehaloses, respectively. In each case, tricyclic 9-oxa-10-boraanthracene-derived borinic acid bearing a dimethyl or bis-trifluoromethyl group exhibits the best catalytic performance for the regio- and stereoselective glycosylation.

已经开发了使用1,2-O-未保护的糖的三种不同类型的有机硼催化的糖基化用于合成1,2-顺式-糖苷。尽管芳基硼酸催化的与糖基受体的脱水偶联以两种异构体的混合物形式提供了热力学控制的产物，但是二芳基硼酸催化的O-三氟乙糖的O-烷基化以高度立体选择性的方式提供了所需的1,2-顺式糖苷。此外，由1,2-糖基二醇和二芳基硼酸组成的三环硼酸酯复合物可有效地促进亚磷酸糖基酯和脱水糖的O-糖基化，分别导致1,1'-β，α-和α，α-海藻糖。在每种情况下，