Work

A Dehydrative Glycosylation Protocol Mediated by Cp2ZrCl2‐AgN(SO2F)2·2MeCN

Year: 2025

Type: article

Abstract: Herein, we report a new dehydrative glycosylation protocol mediated by Cp2ZrCl2‐AgN(SO2F)2·2MeCN combination, which efficiently afforded a diverse array of O‐ and S‐glycosides in good to excellent yields (up to 91% yield). A series of armed pyranosyl and furanosyl donors are shown to be suitable donors, and primary, secondary and tertiary alcohols and aliphatic and aromatic thiols are suitable acceptors. In the absence of external acceptors, self‐condensation could occur to provide a convenient approach to symmetrical 1,1'‐disaccharides. An intriguing rearrangement of 3,4,6‐tri‐O‐benzyl‐2‐deoxy‐D‐glucosose under the Zr promoter system was discovered to provide a C2‐branched pyranose derivatives.

Source: Asian Journal of Organic Chemistry

DOI: 10.1002/ajoc.202500418

Authors: Jia Yu, Yu Tang, Chun Hu, Biao Yu

Institutions: Shenyang Pharmaceutical University, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences

Language: English

Topic: Carbohydrate Chemistry and Synthesis

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: bronze

Funders: National Natural Science Foundation of China, Chinese Academy of Sciences, Youth Innovation Promotion Association of the Chinese Academy of Sciences, Youth Innovation Promotion Association

Awards: G2381777391, G3236379114, G7704625990, G8845658628