3,4-二氰基-2,5,6-三氟苯基苷作为用于化学糖基化的缺电子芴糖基捐赠者

IF 4.4 2区化学 Q2 CHEMISTRY, APPLIED

Advanced Synthesis & Catalysis Pub Date : 2024-11-27 DOI:10.1002/adsc.202401196

Ariza Khanam, Ashwani Tiwari, Mohammad Ovais, Mohan Lal, Pintu Kumar Mandal

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引用次数: 0

摘要

在此，我们介绍了 3,4-二氰基-2,5,6-三氟苯基苷，作为稳定的、反应性强的缺电子氟碳烯基糖基供体，可一步制备并用催化量的 TMSOTf 活化。糖基化反应条件对酸碱敏感的保护基具有耐受性，并且具有不同的底物范围，产率为 68-89%。含氟烯的缺电子糖基供体可以使用游离醇和硅烷化醇以及 C-亲核物作为受体，构建 O-和 C-糖苷。

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3,4‐Dicyano‐2,5,6‐Trifluorophenyl Glycosides as Electron‐Deficient Fluoroarene Glycosyl Donors for Chemical Glycosylation

Here, we present 3,4‐dicyano‐2,5,6‐trifluorophenyl glycosides as bench‐stable, and reactive electron‐deficient fluoroarene based glycosyl donors that can be prepared in one‐step and be activated with catalytic amounts of TMSOTf. The glycosylation reaction conditions show tolerance towards acid/base sensitive protecting groups and have a different substrate scope with 68‐89% yields. The electron‐deficient fluoroarene‐containing glycosyl donor enables the construction of O‐ and C‐glycosides using both free alcohols and silylated alcohols, as well as C‐ nucleophiles as acceptors.

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来源期刊

Advanced Synthesis & Catalysis 化学-应用化学

CiteScore

9.40

自引率

7.40%

发文量

447

审稿时长

1.8 months

期刊介绍： Advanced Synthesis & Catalysis (ASC) is the leading primary journal in organic, organometallic, and applied chemistry. The high impact of ASC can be attributed to the unique focus of the journal, which publishes exciting new results from academic and industrial labs on efficient, practical, and environmentally friendly organic synthesis. While homogeneous, heterogeneous, organic, and enzyme catalysis are key technologies to achieve green synthesis, significant contributions to the same goal by synthesis design, reaction techniques, flow chemistry, and continuous processing, multiphase catalysis, green solvents, catalyst immobilization, and recycling, separation science, and process development are also featured in ASC. The Aims and Scope can be found in the Notice to Authors or on the first page of the table of contents in every issue.