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A comparison of two methods for the preparation of 3‐Deazapurine ribonucleosides
Author(s) -
Montgomery John A.,
Shortnacy Anita T.,
Clayton Sarah D.
Publication year - 1977
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.5570140204
Subject(s) - chemistry , anomer , pyridine , yield (engineering) , trimethylsilyl , bromide , derivative (finance) , medicinal chemistry , stereochemistry , organic chemistry , materials science , economics , financial economics , metallurgy
The reaction of the trimethylsilyl derivative of 4,6‐dichloroimidazo[4,5‐ c ]pyridine with 2,3,5‐tri‐ O ‐benzoyl‐ D ‐ribofuranosyl bromide gave four nucleosides‐the α‐ and β‐anomers of the 1‐isomer and the α‐ and β‐anomers of the 3‐isomer (3.9:2.7:1.5:1). In contrast, the fusion reaction of 4,6‐dichloroimidazo[4,5‐ c ]pyridine with 1,2,3,5‐tetra‐ O ‐acetyl‐β‐ D ‐ribofuranose gave a high yield of the 1‐β‐isomer, which was converted to the known 3‐deazaadenosine (4‐amino‐l‐β‐ D ‐ribofuranosylimidazo[4,5‐ c ]pyridine).
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