Site-Selective Dehydroxy-Chlorination of Secondary Alcohols in Unprotected Glycosides.

ABSTRACT: To circumvent protecting groups, the site-selective modification of unprotected glycosides is intensively studied. We show that site-selective oxidation, followed by treatment of the corresponding trityl hydrazone with tert-butyl hypochlorite and a H atom donor provides an effective way to introduce a chloride substituent in a variety of mono- and disaccharides. The stereoselectivity can be steered, and a new geminal dichlorination reaction is described as well. This strategy challenges existing methods that lead to overchlorination.

SUBMITTER: Zhang J 

PROVIDER: S-EPMC9490796 | biostudies-literature | 2022 Jul

REPOSITORIES: biostudies-literature