SYNTHESIS OF NOVEL 3',4'-SECO ANALOGS OF DIDEHYDRO DIDEOXY NUCLEOSIDES AS POTENTIAL ANTIVIRAL AGENTS

Authors
JOKIC M SKARIC V
Citation
M. Jokic et V. Skaric, SYNTHESIS OF NOVEL 3',4'-SECO ANALOGS OF DIDEHYDRO DIDEOXY NUCLEOSIDES AS POTENTIAL ANTIVIRAL AGENTS, Tetrahedron letters, 35(18), 1994, pp. 2937-2940
Citations number
17
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
35
Issue
18
Year of publication
1994
Pages
2937 - 2940
Database
ISI
SICI code
0040-4039(1994)35:18<2937:SON3AO>2.0.ZU;2-T
Abstract
Novel acyclo analogues (13,14) of didehydro dideoxy adenosine (d4A) la cking C-3'-C-4' bond were synthesized as potential anti-HIV agents. Th e key step involves the bromination of unsaturated isomer 6 with NBS i n mono protected ethylene glycol leading to 3',4'-seco-2'-bromo-3'-hyd roxl compound 11a. Activation of 3'-hydroxy group and reductive elimin ation of vicinal bromo tosylate gave 13 which on deprotection was conv erted into the target molecule 14.