A highly facile and efficient one-step synthesis of N6-adenosine and N6-2'-deoxyadenosine derivatives.
[reaction: see text] A highly facile and efficient one-step synthesis of N6-adenosine and N6-2'-deoxyadenosine derivatives has been developed. Treatment of inosine or 2'-deoxyinosine, without protection of sugar hydroxyl groups, with alkyl or arylamines, in the presence of BOP and DIPEA in DMF, led to the formation of N6-adenosine and N6-2'-deoxyadenosine derivatives in good to excellent yields. Carcinogenic polyaromatic hydrocarbon (PAH) N6-2'-deoxyadenosine adduct 10 and a rare DNA constituent 11 were thus synthesized directly from 2'-deoxyinosine both in 98% yield.
Wan
Zhao-Kui
ZK
Chemical and Screening Sciences, Wyeth Research, 200 Cambridge Park Drive, Cambridge, Massachusetts 02140, USA. zwan@wyeth.com
Binnun
Eva
E
Wilson
Douglas P
DP
Lee
Jinbo
J
D000241:Adenosine / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry; D020650:Combinatorial Chemistry Techniques; D003839:Deoxyadenosines / Q000138:chemical synthesis*; D015394:Molecular Structure
D003839:Deoxyadenosines; D000241:Adenosine