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Syntheses of 5‐amino‐3‐(β‐d‐ribofuranosyl)imidazo [4,5‐b] pyridin‐7‐one (1‐deazaguanosine) and related nucleosides
Author(s) -
Cline Barry L.,
Panzica Raymond P.,
Townsend Leroy B.
Publication year - 1978
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.5570150524
Subject(s) - chemistry , anomer , condensation , stereochemistry , nucleoside , combinatorial chemistry , thermodynamics , physics
The synthesis of 5‐amino‐3‐(β‐D‐ribofuranosyl)imidazo[4,5‐ b ]pyridin‐7‐one (1‐deazaguano‐sine) has been accomplished by three different methods. The 6‐thioguanosine analog 5‐amino‐3‐(β‐D‐ribofuranosyl)imidazo [4,5‐ b ]pyridin‐7‐thione (1‐deaza‐6‐thioguanosine) has been prepared in situ by a reduction of the corresponding disulfide. The synthesis of various nucleoside precursors of the above compounds by several condensation procedures are described. The procedures used to unequivocally determine the site of ribosylation and anomeric configuration are also discussed.