Thiourea-Catalyzed Glycosylation of C,N-Diaryl Glycosyl Imidates

IF 4.7 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2026-10-16 Epub Date: 2026-10-05 DOI:10.1021/acs.orglett.6c03907

Shashiprabha Dubey, Pintu Kumar Mandal

引用次数: 0

Abstract

We report a hydrogen bond-mediated glycosylation protocol employing a new class of C,N-diaryl imidate glycosyl donors bearing two para-fluorophenyl groups, enabling highly efficient and stereoselective glycosylation across a broad range of acceptors. A mechanistic study revealed that thiourea catalysts activate the C,N-diaryl imidate glycosyl donors by forming a noncovalent donor-catalyst complex through hydrogen-bonds. Furthermore, the mild activation conditions and distinct reactivity of C,N-diaryl imidate glycosyl donors facilitate their application in various one-pot oligosaccharide synthesis strategies.

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硫脲催化C，N -二芳基糖基的糖基化

摘要：我们报道了一种氢键介导的糖基化方案，采用了一类新的C， n -二芳酰酰亚咪酯糖基供体，带有两个对氟苯基，在广泛的受体上实现了高效和立体选择性的糖基化。一项机制研究表明，硫脲催化剂通过氢键形成非共价给体-催化剂配合物，从而激活C， n-二芳酰亚咪酯糖基给体。此外，C， n -二芳酰亚咪酯糖基供体具有温和的活化条件和独特的反应活性，有利于其在各种一锅合成低聚糖策略中的应用。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.