NUCLEOSIDES AND NUCLEOTIDES .138. SYNTHESIS OF 3-HALO-3-DEAZAINOSINES- CONFORMATIONAL LOCK WITH THE HALOGEN AT THE 3-POSITION OF THE 3-DEAZAINOSINE IN ANTI-CONFORMATION

Authors
MINAKAWA N KOJIMA N MATSUDA A
Citation
N. Minakawa et al., NUCLEOSIDES AND NUCLEOTIDES .138. SYNTHESIS OF 3-HALO-3-DEAZAINOSINES- CONFORMATIONAL LOCK WITH THE HALOGEN AT THE 3-POSITION OF THE 3-DEAZAINOSINE IN ANTI-CONFORMATION, Heterocycles, 42(1), 1996, pp. 149-154
Citations number
12
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Heterocycles → ACNP
ISSN journal
03855414
Volume
42
Issue
1
Year of publication
1996
Pages
149 - 154
Database
ISI
SICI code
0385-5414(1996)42:1<149:NAN.SO>2.0.ZU;2-1
Abstract
Synthesis of 3-chloro-, bromo-, and iodo-3-deazainosines (6-8) can be done by treatment of the 3-deazainosine derivative (2) with N-halosucc inimides. Treatment of the 5-formylimidazole derivative (11) with viny lmagnesium bromide gave 5-(1-hydroxy-2-propenyl)imidazole derivative ( 12), followed by fluorination and appropriate manipulations to cyclize , affording 3-fluoro-3-deazainosine (18). Although free rotation aroun d the glycosyl linkage in 3-deazainosine (1) and 18 was observed, thos e of 6, 7, and 8 were rather fixed in the anti-conformation as analyze d by nOe experiments.