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Purine nucleosides XVII. The synthesis and conformation of 6‐amino‐9‐ β ‐D‐ribopyranosylpurine and related derivatives prepared via the fusion procedure
Author(s) -
Pan Yung Hsin,
Robins Roland K.,
Townsend Leroy B.
Publication year - 1967
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570040213
Subject(s) - chemistry , purine , purine metabolism , catalysis , proton magnetic resonance , halogenation , stereochemistry , fusion , combinatorial chemistry , organic chemistry , nuclear magnetic resonance , linguistics , physics , philosophy , enzyme
The preparation of 2, 6‐dichloro‐9‐(2′,3′,4′‐tri‐ O ‐acetyl‐β‐D‐ribopyranosyl)purine (I) has been accomplished utilizing the acid catalyzed fusion procedure. The displacement of the 6‐chloro group, or the 2‐ and 6‐chloro group has been studied. Several new 6‐substituted‐9‐(β‐D‐ribopyranosyl)purines have been prepared by catalytic dehalogenation of the corresponding 2‐chloropurine nucleosides. The conformation and configuration of these D‐ribopyranosylpurines has been assigned with the assistance of proton magnetic resonance studies.