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

17 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

@article{ac538d6d0c5d47fc88322815c716bef3,

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

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.",

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

author = "Chen, \{Grace Shiahuy\} and Chen, \{Chien Shu\} and Chien, \{Tun Cheng\} and Yeh, \{Jun Yen\} and Kuo, \{Chia Chi\} and Talekar, \{Rahul Subhash\} and Chern, \{Ji Wang\}",

year = "2004",

doi = "10.1081/NCN-120027904",

language = "English",

volume = "23",

pages = "347--359",

journal = "Nucleosides, Nucleotides and Nucleic Acids",

issn = "1525-7770",

publisher = "Taylor and Francis Ltd.",

number = "1-2",

}

TY - JOUR

T1 - Nucleosides. IX. Synthesis of Purine N3,5′ -Cyclonucleosides and N3,5′-Cyclo-2′,3′ -seconucleosides via Mitsunobu Reaction as TIBO-like Derivativest

AU - Chen, Grace Shiahuy

AU - Chen, Chien Shu

AU - Chien, Tun Cheng

AU - Yeh, Jun Yen

AU - Kuo, Chia Chi

AU - Talekar, Rahul Subhash

AU - Chern, Ji Wang

PY - 2004

Y1 - 2004

N2 - 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.

AB - 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.

KW - Formycin B

KW - Mitsunobu reaction

KW - N ,5′-cyclo-2′, 3′-seconucleoside

KW - N,5′-cyclonucleoside

KW - TIBO

UR - https://www.scopus.com/pages/publications/1542679040

UR - https://www.scopus.com/pages/publications/1542679040#tab=citedBy

U2 - 10.1081/NCN-120027904

DO - 10.1081/NCN-120027904

M3 - Article

C2 - 15043159

AN - SCOPUS:1542679040

SN - 1525-7770

VL - 23

SP - 347

EP - 359

JO - Nucleosides, Nucleotides and Nucleic Acids

JF - Nucleosides, Nucleotides and Nucleic Acids

IS - 1-2

ER -