Direct radical functionalization of native sugars.

ABSTRACT: Naturally occurring (native) sugars and carbohydrates contain numerous hydroxyl groups of similar reactivity^1,2. Chemists, therefore, rely typically on laborious, multi-step protecting-group strategies³ to convert these renewable feedstocks into reagents (glycosyl donors) to make glycans. The direct transformation of native sugars to complex saccharides remains a notable challenge. Here we describe a photoinduced approach to achieve site- and stereoselective chemical glycosylation from widely available native sugar building blocks, which through homolytic (one-electron) chemistry bypasses unnecessary hydroxyl group masking and manipulation. This process is reminiscent of nature in its regiocontrolled generation of a transient glycosyl donor, followed by radical-based

SUBMITTER: Jiang Y 

PROVIDER: S-EPMC11236704 | biostudies-literature | 2024 Jul

REPOSITORIES: biostudies-literature