Synthesis of 3-Deoxy-d-manno-oct-2-ulosonic Acid (KDO) and Pseudaminic Acid C-Glycosides.

ABSTRACT: The preparation of glycosyl dibutyl phosphates in the 3-deoxy-d-manno-oct-2-ulosonic acid (KDO) and pseudaminic acid series and their application to the formation of C-glycosides are described. Both donors were obtained from the corresponding thioglycosides by treatment with dibutylphosphoric acid and N-iodosuccinimide. As with the thioglycosides, both donors adopted very predominantly the strongly electron-withdrawing tg conformation of their side chains, which is reflected in the excellent equatorial selectivity of both donors in the formation of exemplary O-glycosides. With respect to C-glycoside formation on the other hand, contrasting results were observed: the KDO donor was either relatively unselective or selective for the formation of the a

SUBMITTER: Onobun E 

PROVIDER: S-EPMC7749074 | biostudies-literature | 2020 Dec

REPOSITORIES: biostudies-literature