Regiodivergent Functionalization of Protected and Unprotected Carbohydrates via an Adaptive Activating Strategy

02 July 2024, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

The selective functionalization of carbohydrates holds a central position in synthetic carbohydrate chemistry, driving the ongoing quest for ideal approaches to manipulate these compounds. In this study, we introduce a general strategy that enables the regiodivergent functionalization of saccharides. The use of electron-deficient photoactive 4-tetrafluoropyridinylthio (SPyf) fragment as an adaptable activating group, facilitated efficient functionalization across all saccharide sites. More importantly, this activating group can be directly installed at the C1, C5 and C6 positions of biomass-derived carbohydrates in a single step and in a site-selective manner, allowing for the efficient and precision-oriented modification of unprotected saccharides and glycans.

Keywords

carbohydrate chemistry
selective functionalization
unprotected saccharides

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