Exploring the Dual Functions of Distal Acyl Group Direction in Various Nucleophilic Environments

Yongtao Gao, Wenjie Chen, Juan Zhao, Min Yang, Yongliang Zhang, Changsheng Chen, Linbin Yao, Jiayuan Xu, Fei Wang, Bangzhi Zhang, Guofeng Gu, Bencan Tang, Feng Cai

Research output: Journal PublicationArticlepeer-review


A universal glycosylation strategy could significantly simplify glycoside synthesis. One approach to achieving this goal is through acyl group direction for the corresponding 1,2-, 1,3-, 1,4-, or 1,6-trans glycosylation; however, this approach has been challenging for glycosidic bonds that require distal equatorial-acyl group direction. We developed an approach in weakly nucleophilic environments for selective 1,4-trans glycosylation directed by the equatorial-4-O-acyl group. Here, we explored this condition in other distal acyl groups and found that, besides 1,n-trans direction, acyl groups also mediated hydrogen bonding between acyl groups and alcohols. The latter showed a diverse effect and classified the acyl group direction into axial and equatorial categories. Corresponding glycosylation conditions were distinguished as guidance for acyl group direction from either category. Hence, acyl group direction may serve as a general glycosylation strategy.

Original languageEnglish
Pages (from-to)2375-2396
Number of pages22
JournalJournal of Organic Chemistry
Issue number4
Publication statusPublished - 16 Feb 2024

ASJC Scopus subject areas

  • Organic Chemistry


Dive into the research topics of 'Exploring the Dual Functions of Distal Acyl Group Direction in Various Nucleophilic Environments'. Together they form a unique fingerprint.

Cite this