[Au]/[Ag]-Catalyzed Glycosidation of Ethynylcyclohexyl Glycosyl Carbonates Enables Direct Stereoselective Synthesis of 2-Azido-2-deoxy-β-mannopyranosides

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2024-12-09 DOI:10.1021/acs.orglett.4c0420810.1021/acs.orglett.4c04208

Pratim Kumar Das, Daniil A. Ahiadorme, Niteshlal Kasdekar, Jayashree Rajput, Madhuri Vangala, David Crich* and Srinivas Hotha*,

引用次数: 0

Abstract

We describe the [Au]/[Ag]-catalyzed activation of ethynylcyclohexyl 2-azido-4,6-O-benzylidene mannosyl carbonates for β-mannosamine linkage preparation in high yield and selectivity in a temperature- and concentration-dependent manner. VT-NMR studies reveal an anomeric triflate intermediate generated in the absence of an acceptor alcohol that is stable up to −10 °C. The generality of the protocol was illustrated by successful application to a series of acceptors and by synthesis of a fully protected Streptococcus pneumoniae type 19F capsular trisaccharide.

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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.