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A convenient synthesis of certain 1‐(β‐D‐ribofuranosyl)benzotriazoles
Author(s) -
Revankar Ganapathi R.,
Townsend Leroy B.
Publication year - 1968
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.5570050608
Subject(s) - chemistry , benzotriazole , yield (engineering) , bromide , anomer , condensation , medicinal chemistry , acetylation , stereochemistry , combinatorial chemistry , organic chemistry , biochemistry , materials science , physics , gene , metallurgy , thermodynamics
The synthesis of 5,6‐dichloro‐1‐(β‐ D ‐ribofuranosyl)benzotriazole ( 4a ), 5,6‐dimethyl‐1‐(β‐ D ‐ribofuranosyl)benzotriazole ( 4b ) and 1‐(β‐ D ‐ribofuranosyl)benzotriazole ( 4c ) in good yield has been accomplished by the condensation of the appropriate 1‐trimethylsilylbenzotriazole ( 1a, 1b , and 1c ) with 2,3,5‐tri‐ O ‐acetyl‐ D ‐ribofuranosyl bromide (2) followed by subsequent deacetylation of the reaction products. The assignment of anomeric configuration and site of glycosidation for all nucleosides reported is discussed.