Photoinitiated Thiol-Ene Reactions of Various 2,3-Unsaturated O-, C- S- and N-Glycosides - Scope and Limitations Study.

ABSTRACT: The photoinitiated thiol-ene addition reaction is a highly stereo- and regioselective, and environmentally friendly reaction proceeding under mild conditions, hence it is ideally suited for the synthesis of carbohydrate mimetics. A comprehensive study on UV-light-induced reactions of 2,3-unsaturated O-, C-, S- and N-glycosides with various thiols was performed. The effect of experimental parameters and structural variations of the alkenes and thiols on the efficacy and regio- and stereoselectivity of the reactions was systematically studied and optimized. The type of anomeric heteroatom was found to profoundly affect the reactivity of 2,3-unsaturated sugars in the thiol-ene couplings. Hydrothiolation of 2,3-dideoxy O-glycosyl enosides efficiently produced the axially C2-S-substituted addit

SUBMITTER: Kelemen V 

PROVIDER: S-EPMC7154673 | biostudies-literature | 2020 Mar

REPOSITORIES: biostudies-literature