Regioselective silyl/acetate exchange of disaccharides yields advanced glycosyl donor and acceptor precursors.

ABSTRACT: Glycoconjugates are composed of carbohydrate building blocks linked together in a multitude of ways giving rise to diverse biological functions. Carbohydrates are especially difficult to synthetically manipulate because of the similar reactivity of their numerous and largely equivalent hydroxyl groups. Hence, methodologies for both the efficient protection and selective modification of carbohydrate alcohols are considered important synthetic tools in organic chemistry. When per-O-TMS protected mono- or disaccharides in a mixture of pyridine and acetic anhydride are treated with acetic acid, regioselective exchange of silicon for acetate protecting groups occurs. Acid concentration, thermal conditions, and microwave assistance mediate the silyl/acetate exchange reaction. Regiocontrol is ach

SUBMITTER: Hsieh HW 

PROVIDER: S-EPMC4492524 | biostudies-literature | 2013 Oct

REPOSITORIES: biostudies-literature