Stereoselective Synthesis of d‑5-Homo-4-selenoribose as a Versatile Intermediate for 4′-Selenonucleosides

Stereoselective Synthesis of d‑5-Homo-4-selenoribose as a Versatile Intermediate for 4′-Selenonucleosides

Stereoselective synthesis of d-5-homo-4-selenoribose, serving as a versatile intermediate for the synthesis of 4′-selenonucleosides 12a–c, was accomplished using Sharpless asymmetric epoxidation, regioselective cleavage of the α,β-epoxide, and stereoselective reduction of the ketone as the key steps...

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Veröffentlicht in:Organic letters 2015-09, Vol.17 (18), p.4636-4639
Hauptverfasser: Kim, Gyudong, Choi, Yoojin, Sahu, Pramod K, Yu, Jinha, Qu, Shuhao, Lee, Dongjoo, Jeong, Lak Shin
Format: Artikel
Sprache:eng
Schlagworte:
Epoxy Compounds - chemistry
Molecular Structure
Nucleosides - chemical synthesis
Nucleosides - chemistry
Organoselenium Compounds - chemical synthesis
Organoselenium Compounds - chemistry
Stereoisomerism
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Zusammenfassung:Stereoselective synthesis of d-5-homo-4-selenoribose, serving as a versatile intermediate for the synthesis of 4′-selenonucleosides 12a–c, was accomplished using Sharpless asymmetric epoxidation, regioselective cleavage of the α,β-epoxide, and stereoselective reduction of the ketone as the key steps.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.5b02393