Synthesis and anti-HIV activity of 2-substituted 2'-deoxy-2'- fluoroadenosines

Article abstract of DOI:10.1080/15257779408012146

2-Iodo-6-methoxypurine 2'-deoxy-2'-fluororiboside 8 was prepared from 2- iodo-6-methoxypurine riboside 1 in 8 steps. Reaction of 8 with ammonia in methanol gave the 2-iodoadenosine derivative 9 in 69% yield. Treatment of 9 with various nucleophiles gave 2-substituted analogues of 2'-deoxy-2'- fluoroadenosine 10-12. 2'-Deoxy-2,2'-difluoroadenosine 14 was also prepared by the treatment of the quaternary salt 13 with fluoride ion, but similar reactions of 13 with chloride or bromide ion gave the corresponding piperidine congeners 15a,b.

Full text of DOI:10.1080/15257779408012146

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Synthesis and Anti-HIV Activity
of 2-Substituted 2′-Deoxy-2′-
fluoroadenosines
a
a
a
Tokumi Maruyama , Kunihiko Utsumi , Yoshiko Sato & Douglas D.
b
Richman
a
Department of Pharmaceutical Sciences , Tokushima Bunri
University , Yamashiro-cho, Tokushima, 770, JAPAN
b
Departments of Pathology and Medicine , University of California ,
San Diego, La Jolla, California, 92093-0679, U.S.A.
Published online: 24 Sep 2006.
To cite this article: Tokumi Maruyama , Kunihiko Utsumi , Yoshiko Sato & Douglas D. Richman (1994)
Synthesis and Anti-HIV Activity of 2-Substituted 2′-Deoxy-2′-fluoroadenosines, Nucleosides and
Nucleotides, 13:6-7, 1219-1230, DOI: 10.1080/15257779408012146
To link to this article: http://dx.doi.org/10.1080/15257779408012146
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