Introduction of Fluorine Into the C8 Position of Purine Nucleosides
- 1 February 1990
- journal article
- research article
- Published by Taylor & Francis in Nucleosides, Nucleotides and Nucleic Acids
- Vol. 9 (2) , 197-204
- https://doi.org/10.1080/07328319008045132
Abstract
We have synthesized 2-amino-6,8-difluoro-9-(2,3,5-tri-O-acetyl-.beta.-D-ribofuranosyl)purine (3) from 2-amino-6,8-dichloro-9-(2,3,5-tri-O-acetyl-.beta.-D-ribofuranosyl)purine (1) in a two-step procedure. The reaction of 3 with anhydrous ammonia in dry 1,2-dimethoxyethane gave 2,8-diamino-6-fluoro-9-(2,3,5-tri-O-acetyl-.beta.-D-ribofuranosyl)purine (1) in a two-step procedure. The reaction of 3 with anhydrous ammonia in dry 1,2-dimethoxyethane gave 2,8-diamino-6-fluoro-9-(2,3,5-tri-O-acetyl-.beta.-D-ribofuranosyl)purien (4) in 64.1% yield. Compound 4 was deaminated with t-butylnitrite in tetrahydrofuran to give 2-amino-6-fluoro-9-(2,3,5-trio-O-acetyl-.beta.-D-ribofuranosyl)purine (6). The 1H, 19F, and 13C NMR spectral data were determined and evaluated for eah of the compounds.This publication has 24 references indexed in Scilit:
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