Nucleosides. IX. Synthesis of Purine N3,5′ -Cyclonucleosides and N3,5′-Cyclo-2′,3′ -seconucleosides via Mitsunobu Reaction as TIBO-like Derivativest

Grace Shiahuy Chen; Chien Shu Chen; Tun Cheng Chien; Jun Yen Yeh; Chia Chi Kuo; Rahul Subhash Talekar; Ji Wang Chern

doi:10.1081/NCN-120027904

Nucleosides. IX. Synthesis of Purine N³,5′ -Cyclonucleosides and N³,5′-Cyclo-2′,3′ -seconucleosides via Mitsunobu Reaction as TIBO-like Derivativest

Grace Shiahuy Chen, Chien Shu Chen, Tun Cheng Chien, Jun Yen Yeh, Chia Chi Kuo, Rahul Subhash Talekar, Ji Wang Chern^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

16 Citations (Scopus)

Abstract

The Mitsunobu reaction was applied to prepare, in one step, purine N ³,5′-cyclonucleosides 10a-d. A subsequent ring opening in the ribose moiety of the resultant N³,5′-nucleosides by sodium periodate led to the corresponding N³,5′-cyclo-2′ ,3′-seconucleosides. These products consist of 5-, 6-, and 7-membered tricyclic system which is the basic skeleton of TIBO derivatives, known antiviral agents.

Original language	English
Pages (from-to)	347-359
Number of pages	13
Journal	Nucleosides, Nucleotides and Nucleic Acids
Volume	23
Issue number	1-2
DOIs	https://doi.org/10.1081/NCN-120027904
Publication status	Published - 2004
Externally published	Yes

Keywords

Formycin B
Mitsunobu reaction
N ,5′-cyclo-2′, 3′-seconucleoside
N,5′-cyclonucleoside
TIBO

ASJC Scopus subject areas

Biochemistry
Molecular Medicine
Genetics

Access to Document

10.1081/NCN-120027904

Cite this

Nucleosides. IX. Synthesis of Purine N³,5′ -Cyclonucleosides and N³,5′-Cyclo-2′,3′ -seconucleosides via Mitsunobu Reaction as TIBO-like Derivativest. / Chen, Grace Shiahuy; Chen, Chien Shu; Chien, Tun Cheng et al.
In: Nucleosides, Nucleotides and Nucleic Acids, Vol. 23, No. 1-2, 2004, p. 347-359.

Research output: Contribution to journal › Article › peer-review

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abstract = "The Mitsunobu reaction was applied to prepare, in one step, purine N 3,5′-cyclonucleosides 10a-d. A subsequent ring opening in the ribose moiety of the resultant N3,5′-nucleosides by sodium periodate led to the corresponding N3,5′-cyclo-2′ ,3′-seconucleosides. These products consist of 5-, 6-, and 7-membered tricyclic system which is the basic skeleton of TIBO derivatives, known antiviral agents.",

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AU - Chen, Grace Shiahuy

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AU - Talekar, Rahul Subhash

AU - Chern, Ji Wang

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