Stereoselective Approach for the Synthesis of Diverse 1′-Modified Carbanucleosides

Stereoselective Approach for the Synthesis of Diverse 1′-Modified Carbanucleosides

We describe an efficient and stereoselective synthesis of 1'-substituted-β-carbocylic nucleosides 5 via gem-dichlorooxirane intermediate 7, which directly condensed with weak nucleophiles such as pyrimidines or purines. The formation of gem-dichlorooxirane 7 and direct nucleobase condensation e...

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Bibliographic Details
Published in:Organic letters Vol. 25; no. 46; pp. 8377 - 8381
Main Authors: Sung, Kisu, Aswar, Vikas R., Song, Jiyoon, Jarhad, Dnyandev B., Jeong, Lak Shin
Format: Journal Article
Language:English
Published: 24-11-2023
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Summary:We describe an efficient and stereoselective synthesis of 1'-substituted-β-carbocylic nucleosides 5 via gem-dichlorooxirane intermediate 7, which directly condensed with weak nucleophiles such as pyrimidines or purines. The formation of gem-dichlorooxirane 7 and direct nucleobase condensation exclusively proceeded in protic polar solvents like MeOH. This method provides a general and modular route for the late-stage diversification of 1'-modified nucleosides.
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.3c03518