ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The syntheses of 2′,3′-dideoxy-2′,3′-didehydro-β-D-ribofuranoside 1 and 2′,3′-dideoxy-3′-fluoro-β-D-ribo-furanoside 5 of 7-deazaguanine as well as 7-deaza-2′-deoxyxyloguanosine (3) are described. The corresponding 2,4-diamino compounds 2 and 4 were also prepared. Thus, silytation of 2-amino-4-chloro-7-(2-deoxy-β-D-erythro-pentofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine (6) afforded 7, which gave the oxo-nucleoside 13 after oxidation with CrO3. NaBH4 reduction yielded 14 which, upon deprotection (Bu4NF) and nucieophific displacement, afforded 3 and 4. On the other hand, the N2-formyl derivative of 7 was mesylated (→ 10), treated with Bu4NF, and deprotected with NH3 yielding the 2′,3′-dideoxy-2′,3′-didehydro-nucleoside 12, Nucleophilic displacement reactions on 12 yielded 1 and 2. The fluoro-nucleoside 5 was obtained from 14 after methoxytritylation of the NH2 group (→ 16), fluorination with DAST (→ 17), and treatment with 2M NaOH. The 5′-triphosphates of 5 and other pyrrolo[2,3-d]pyrimidine 2′,3′-dideoxy-3′-fluoro-nucleosides were found to be highly active inhibitors of HIV-1. reverse transcriptase, similar to those of 1 and 2.
Additional Material:
1 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19910740517
