Work

Activation of Thioglycosides with Ferric Chloride: Scope and Mechanism

Year: 2026

Type: article

Abstract: Previously, we disclosed a new method for the activation of armed and superarmed ethylthio glycosides using an inexpensive and abundant iron-(III) chloride. Reported herein are the next steps toward refining the reaction conditions, broadening the scope of this method to glycosidation of less-reactive glycosyl donors, and investigating the reaction mechanism. This reaction is swift and generally high-yielding. The completion of the reaction can be monitored by eye, and typically, the color change (start of the reaction) can be detected right after the addition of the glycosyl donor to the premixed mixture of the acceptor and ferric chloride.

Source: ACS Omega

DOI: 10.1021/acsomega.6c03149

Authors: Lacie M. Ridgway, Rachel L. Turecki, Faranak Pooladian, Anupama Das, Alexei V. Demchenko

Institution: Saint Louis University

Language: English

Topic: Carbohydrate Chemistry and Synthesis

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: gold

Estimated APC paid: $1,935

Funder: National Institutes of Health