Stereoselective synthesis of 3-oxo-2-C-branched glycosides from 2,3-unsaturated sugars via [3,3]-sigmatropic rearrangement†

IF 2.7 3区 化学 Q1 CHEMISTRY, ORGANIC Organic & Biomolecular Chemistry Pub Date : 2025-01-16 Epub Date: 2025-01-23 DOI:10.1039/d4ob01769b
Intzar Ali , Sravani Gundumalla , Ramu Sridhar Perali
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Abstract

A number of monosaccharide-derived glycals were initially converted to the corresponding 3-O-allyl 2,3-unsaturated glycosides and then subjected to Claisen rearrangement to produce 3-oxo-2-C-branched sugar derivatives with good to excellent stereoselectivity. The methodology was extended to synthesize allyl vinyl ethers derived from disaccharides. The application of the developed protocol was showcased by synthesizing the bicyclic core unit of the iridoid frameworks.

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2,3-不饱和糖[3,3]异位重排立体选择性合成3-氧-2- c支链糖苷。
许多单糖衍生的糖基首先转化为相应的3-o -烯丙基2,3-不饱和糖苷,然后进行Claisen重排,得到立体选择性好的3-o -2- c支链糖衍生物。该方法扩展到合成由双糖衍生的烯丙基乙烯醚。通过合成环烯醚萜骨架的双环核心单元,展示了该方案的应用。
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来源期刊
Organic & Biomolecular Chemistry
Organic & Biomolecular Chemistry 化学-有机化学
CiteScore
5.50
自引率
9.40%
发文量
1056
审稿时长
1.3 months
期刊介绍: Organic & Biomolecular Chemistry is an international journal using integrated research in chemistry-organic chemistry. Founded in 2003 by the Royal Society of Chemistry, the journal is published in Semimonthly issues and has been indexed by SCIE, a leading international database. The journal focuses on the key research and cutting-edge progress in the field of chemistry-organic chemistry, publishes and reports the research results in this field in a timely manner, and is committed to becoming a window and platform for rapid academic exchanges among peers in this field. The journal's impact factor in 2023 is 2.9, and its CiteScore is 5.5.
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