N-(para-Methoxyphenylpropargyl) Pyrrole-2-carboxylate (PPPC) Glycosides as Donors for Glycosylation

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC Organic Letters Pub Date : 2024-12-24 DOI:10.1021/acs.orglett.4c04389

Li Song, Meifang Yang, Mengyu Li, Yanli Qiu, Yili Dai, Jingyu Tian, Xing Zheng, Yitian Zhao, Xu Yao, Houchao Tao

引用次数: 0

Abstract

We developed glycosyl N-(para-methoxyphenylpropargyl) pyrrole-2-carboxylates (PPPCs) as highly effective donors for chemical glycosylation. The modular design and exceptional stability of the acid precursor provide PPPC donors with synthetic versatility and ease of use. Activated by NIS/TMSOTf, PPPC donors exhibit a broad compatibility for both O- and N-glycosylation reactions. Their distinct reactivity gradient enables streamlined one-pot syntheses, complementing thioglycosides and imidates. These features position PPPC donors as promising tools for advancing carbohydrate chemistry.

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N-（对甲氧基苯基丙炔）吡咯-2-羧酸（PPPC）糖苷作为糖基化供体

我们开发了糖基N-（对甲氧基苯基丙炔）吡咯-2-羧酸酯（PPPCs）作为化学糖基化的高效供体。酸前体的模块化设计和卓越的稳定性为PPPC供体提供了合成的多功能性和易用性。在NIS/TMSOTf的激活下，PPPC供体对O-和n -糖基化反应表现出广泛的兼容性。其独特的反应性梯度使流线型的一锅合成，补充巯基糖苷和拟合物。这些特点使PPPC捐助者成为推进碳水化合物化学的有前途的工具。

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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.

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