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Nucleosides XII. 1 Synthesis of 5‐Modified Isoguanosines and Reinvestigation of 5′‐Deoxy‐ N 3 ,5′‐cycloisoguanosine
Author(s) -
Chien TunCheng,
Kuo ChiaChi,
Chen ChienShu,
Chern JiWang
Publication year - 2004
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.200400205
Subject(s) - chemistry , thionyl chloride , pyridine , carbon tetrachloride , aqueous solution , medicinal chemistry , chloride , base (topology) , derivative (finance) , tetrachloride , stereochemistry , organic chemistry , mathematical analysis , mathematics , tin , financial economics , economics
Isoguanosine ( 3 ) underwent a coupling reaction with diaryl disulfides in the presence of tri‐ n ‐butylphosphine when its 6‐amino group was protected by N,N ‐dimethylaminomethylidene. The synthesis of 5′‐deoxy‐ N 3 ,5′‐cycloisoguanosine ( 6 ) and its 2′,3′‐ O ‐isopropylidene derivative ( 11 ) were accomplished in excellent yields from isoguanosines ( 3 & 10 ) in the presence of triphenylphospine and carbon tetrachloride in pyridine. Chlorination at the 5′‐position of isoguanosine ( 3 ) with thionyl chloride followed by the aqueous base‐promoted cyclization afforded the same product 6 . The structures were elucidated by spectroscopic analysis including IR, UV, 1‐D and 2‐D NMR.