Palladium-Catalyzed Glycosylation for the Highly Stereoselective de Novo Construction of Trideoxy Glycan Motifs from Pyridapeptides B-E.

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-10-02 DOI:10.1021/acs.orglett.5c03679

Rui Su,Guozhi Xiao

引用次数: 0

Abstract

Highly stereocontrolled synthesis of tetrasaccharides with 2,3,6-trideoxy rhodinose and amicetose motifs from pyridapeptides D and E has been achieved for the first time. A trideoxy monosaccharide in pyridapeptide B and trideoxy disaccharide in pyridapeptide C were also prepared for structure-activity relationship studies. Synthetic routes feature the following steps: 1) de novo synthesis of glycosyl ester through RhIII-catalyzed asymmetric transfer hydrogenation, Achmatowicz rearrangement, and (S)-BTM-catalyzed acylation; 2) palladium-catalyzed glycosylation for construction of all trideoxyglycosidic linkages; 3) chiral catalyst-controlled tandem reductions of enones.

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钯催化糖基化以高立体选择性地从吡啶肽B-E中重新构建三脱氧聚糖基序。

本文首次以吡啶肽D和E为原料合成了具有2,3,6-三脱氧罗丹糖和氨基糖基序的高立体控制的四糖。同时制备了吡喃肽B的三脱氧单糖和吡喃肽C的三脱氧双糖，并进行了构效关系的研究。合成路线如下：1)通过rhiii催化的不对称转移氢化、Achmatowicz重排和(S)- btm催化的酰化，重新合成糖基酯；2)钯催化糖基化构建所有三脱氧糖苷键；3)手性催化剂控制的烯酮串联还原。

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.