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通过催化应变释放实现与-2,2-二甲氧基羰基环丙基苄基硫代糖苷供体的高效糖基化反应。

Efficient - and -glycosylation with -2,2-dimethoxycarbonylcyclopropylbenzyl thioglycoside donors by catalytic strain-release.

作者信息

Ding Han, Lv Jian, Zhang Xiao-Lin, Xu Yuan, Zhang Yu-Han, Liu Xue-Wei

机构信息

School of Chemistry, Chemical Engineering and Biotechnology, Nanyang Technological University 21 Nanyang Link 637371 Singapore

Key Laboratory of Marine Drugs of Ministry of Education, Shandong Key Laboratory of Glycoscience and Glycotechnology, School of Medicine and Pharmacy, Ocean University of China Qingdao Shandong 266003 China.

出版信息

Chem Sci. 2024 Feb 7;15(10):3711-3720. doi: 10.1039/d3sc06619c. eCollection 2024 Mar 6.

DOI:10.1039/d3sc06619c
PMID:38455029
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC10915852/
Abstract

We herein present a strain-release glycosylation method employing a rationally designed -2,2-dimethoxycarbonylcyclopropylbenzyl (CCPB) thioglycoside donor. The donor is activated through the nucleophilic ring-opening of a remotely activable donor-acceptor cyclopropane (DAC) catalyzed by mild Sc(OTf). Our new glycosylation method efficiently synthesizes -, -, and -glycosides, providing facile chemical access to the challenging -glycosides. Because the activation conditions of conventional glycosyl donors and our CCPB thioglycoside are orthogonal, our novel donor is amenable to controlled one-pot glycosylation reactions with conventional donors for expeditious access to complex glycans. The strain-release glycosylation is applied to the assembly of a tetrasaccharide of -polysaccharide of O-33 in one pot and the synthesis of a 1,1'-S-linked glycoside oral galectin-3 (Gal-3) inhibitor, TD139, to demonstrate the versatility and effectiveness of the novel method for constructing both - and -glycosides.

摘要

我们在此介绍一种利用合理设计的 -2,2-二甲氧基羰基环丙基苄基（CCPB）硫代糖苷供体的应变释放糖基化方法。该供体通过温和的Sc(OTf)催化的远程可活化供体-受体环丙烷（DAC）的亲核开环反应而被活化。我们的新糖基化方法能够高效合成α-、β-和γ-糖苷，为具有挑战性的β-糖苷提供了便捷的化学合成途径。由于传统糖基供体和我们的CCPB硫代糖苷的活化条件相互正交，我们的新型供体适用于与传统供体进行可控的一锅法糖基化反应，以便快速合成复杂聚糖。应变释放糖基化反应被应用于一锅法组装O-33的α-多糖四糖以及合成1,1'-S-连接的糖苷口服半乳糖凝集素-3（Gal-3）抑制剂TD139，以证明该新方法在构建α-和β-糖苷方面的通用性和有效性。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b48e/10915852/a67305306fe9/d3sc06619c-f8.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b48e/10915852/a67305306fe9/d3sc06619c-f8.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b48e/10915852/b8190ba49f75/d3sc06619c-f1.jpg
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