Stereoselective Synthesis of β-glycosyl Esters via 1-Hydroxybenzotriazole Mediated Acylation of Glycosyl Hemiacetals

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2023-07-12 DOI:10.1021/acs.orglett.3c01750

Zijing Liu, Dan Liu, Dapeng Zhu* and Biao Yu*,

引用次数: 0

Abstract

Highly stereoselective access to β-glycosyl esters was disclosed, employing 1-hydroxybenzotriazole (HOBt) mediated esterification of glycosyl hemiacetals in the presence of EDCI and 1,4-diazabicyclo[2.2.2]octane (DABCO). Mechanistic studies indicated a dynamic kinetic acylation pathway. In addition, a stereoretentive esterification of glycosyl hemiacetals with tert-butyloxycarbonyl ortho-hexynylbenzoate and DMAP was also reported.

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1-羟基苯并三唑介导的糖基半缩醛酰化立体选择性合成β-糖基酯

利用1-羟基苯并三唑(HOBt)介导的糖基半缩醛在EDCI和1,4-重氮比环[2.2.2]辛烷(DABCO)存在下的酯化反应，揭示了β-糖基酯的高度立体选择性通路。机理研究表明这是一个动态的动力学酰化途径。此外，还报道了糖基半缩醛与叔丁氧羰基邻己基苯甲酸酯和DMAP的立体保持酯化反应。

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.