Open AccessSynthesis of 4′-substituted cordycepins
Author(s) -
Yutaka Kubota,
Mayumi Kunikata,
Rumi Ohsawa,
Yuria Odajima,
Kazuhiro Haraguchi,
Hiromichi Tanaka
Publication year - 2005
Publication title -
nucleic acids symposium series
Language(s) - Uncategorized
Resource type - Journals
eISSN - 1746-8272
pISSN - 0261-3166
DOI - 10.1093/nass/49.1.111
Subject(s) - cordycepin , electrophile , chemistry , silylation , nucleophilic substitution , reagent , benzoic acid , organosilicon , electrophilic substitution , nucleophile , acid hydrolysis , hydrolysis , stereochemistry , combinatorial chemistry , organic chemistry , catalysis , biochemistry
Synthesis of 4'-substituted analogues of cordycepin was carried out. Electrophilic addition of N-iodosuccinimide/benzoic acid to 2',5'-bis-O-(tert-butyldimethyl-silyl)-3',4'-unsaturated adenosine (5) enabled the introduction of a leaving group to the 4'-position. The resulting product 7 was converted to 4'-(benzoyloxy) cordycepin (8) upon removal of the 3'-iodine atom. Compound 8 serves as a common precursor for the synthesis of the title compounds through nucleophilic substitution using organoaluminum and organosilicon reagents.
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