ph3po调控Kdo糖苷化合成含β-Kdo双糖的立体选择性研究

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2024-11-30 DOI:10.1021/acs.orglett.4c04193

He Miao, Rurong Yu, Jibin Zheng, Jintao Shang, Lvfeng Zhang, Minghui Ma, You Yang

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引用次数: 0

摘要

提出了一种ph3po调制的β-选择性Kdo糖苷化方法，用于立体选择性合成β-Kdo糖苷。在Ph3PAuOTf和Ph3PO存在下，在低温下与一系列醇在甲苯中进行糖基化反应，得到具有良好至优异β选择性的Kdo糖苷。此外，ph3po调制的方法有效地应用于β-(2→4)-和β-(2→8)-连接的Kdo-Kdo双糖的合成，为进一步的生物学研究提供了基础。

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Ph3PO-Modulated Kdo Glycosidation for Stereoselective Synthesis of β-Kdo-Containing Disaccharides

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Ph3PO-Modulated Kdo Glycosidation for Stereoselective Synthesis of β-Kdo-Containing Disaccharides

A Ph₃PO-modulated β-selective Kdo glycosidation approach is developed for the stereoselective synthesis of β-Kdo glycosides. With the readily available per-O-acetylated Kdo ynenoate as the donor, the glycosylation with a series of alcohols in the presence of Ph₃PAuOTf and Ph₃PO in toluene at low temperatures afforded the desired Kdo glycosides with good to excellent β-selectivities. Furthermore, the Ph₃PO-modulated approach was effectively applied to the synthesis of β-(2→4)- and β-(2→8)-linked Kdo-Kdo disaccharides for further biological studies.

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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.