Development of Glycosylation Protocols Using Glycosyl N-Phenylethynyl Pyrrole-2-carboxylates as Donors

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC Organic Letters Pub Date : 2024-11-12 DOI:10.1021/acs.orglett.4c03768

Mengyu Li, Li Song, Liya Yang, Yitian Zhao, Meifang Yang, Houchao Tao

引用次数: 0

Abstract

We herein introduce glycosyl N-phenylethynyl pyrrole-2-carboxylates (PEPCs) as novel and highly efficient glycosyl donors. The unique inclusion of the pyrrole group, serving as both an electron-donating group and an ortho-tethering scaffold, imparts exceptional shelf stability while retaining reactivity for glycosylation reactions. PEPC donors exhibit broad utility for both O- and N-glycosylation across a variety of substrates. Additionally, their versatility and efficiency were further demonstrated in a one-pot saccharide synthesis, showcasing their potential for diverse synthetic applications.

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使用 N-苯乙炔基吡咯-2-羧酸糖基化协议作为供体的开发

我们在此介绍作为新型高效糖基供体的 N-苯乙炔基吡咯-2-羧酸糖基化物（PEPCs）。独特的吡咯基团既是电子供体，又是正交系链支架，在保持糖基化反应活性的同时，还具有优异的货架稳定性。PEPC 给体在多种底物的 O 型和 N 型糖基化反应中都具有广泛的用途。此外，它们的多功能性和高效性在一次糖合成中得到了进一步证明，展示了它们在各种合成应用中的潜力。

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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.