4-(2′-Phenylethynylphenyl)phenyl glycosides as glycosylation donors-Reference-Cited by-同舟云学术

4-(2′-Phenylethynylphenyl)phenyl glycosides as glycosylation donors

Published:2023-04-06 Issue:9 Volume:95 Page:965-970
ISSN:0033-4545
Container-title:Pure and Applied Chemistry
language:en
Short-container-title:

Author:

Liu Wei¹,Wang Ziqiang²,Gulzar Tayyab²,Zhang Xiaodong²,Ding Guoping²,Xu Peng¹^ORCID,Yu Biao²^ORCID

Affiliation:

1. School of Physical Science and Technology , ShanghaiTech University , 100 Haike Road , Shanghai 201210 , China

2. State Key Laboratory of Bioorganic and Natural Products Chemistry , Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Road , Shanghai 200032 , China

Abstract

Abstract We have disclosed that 3,5-dimethyl-4-(2′-phenylethynylphenyl)phenyl (EPP) glycosides could be employed as glycosylation donors via an unprecedented activation mechanism. Here we report that the EPP glycosides without the 3,5-dimethyl groups, which were previously installed to prevent the plausible Friedel-Crafts-type side reactions, can also undergo glycosylation effectively. Employing such an EPP 2-azidoglucoside as donor, the construction of the challenging α-GlcN-(1→4)-GlcA linkage is realized, leading to a heparin trisaccharides precursor.

Funder

Key Research Program of Frontier Sciences of CAS

Youth Innovation Promotion Association of CAS

Shanghai Municipal Science and Technology Major Project

National Natural Science Foundation of China

Publisher

Walter de Gruyter GmbH

Subject

General Chemical Engineering,General Chemistry

Link

https://www.degruyter.com/document/doi/10.1515/pac-2022-1114/pdf

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