Synthesis of N6 ,N6-Dialkyl Adenine Nucleosides With In Situ Formed Hexaalkylphosphorus Triamides

Reactions between secondary amines and phosphorus trichloride (PCl 3 ) leads to the formation of the corresponding tris(dialkylamino)phosphines or hexaalkylphosphorus triamides [HAPT: (R 2 N) 3 P]. Reaction of silyl-protected 2′-deoxyinosine and acetyl-protected inosine with the in situ formed HAPT...

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Bibliographic Details
Published in:European journal of organic chemistry 2008-11, Vol.2009 (1), p.152-159
Main Authors: Lakshman, Mahesh K., Choudhury, Asad, Bae, Suyeal, Rochttis, Eliezer, Pradhan, Padmanava, Kumar, Amit
Format: Article
Language:English
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Summary:Reactions between secondary amines and phosphorus trichloride (PCl 3 ) leads to the formation of the corresponding tris(dialkylamino)phosphines or hexaalkylphosphorus triamides [HAPT: (R 2 N) 3 P]. Reaction of silyl-protected 2′-deoxyinosine and acetyl-protected inosine with the in situ formed HAPT and iodine (I 2 ) leads to the formation of N 6 , N 6 -dialkyl adenosine and 2′-deoxyadenosine. In some cases the stoichiometry of the amine is important as also the use of a tertiary amine base. The effect of amine stoichiometry on the reaction of HAPT with I 2 has been studied by 31 P{ 1 H} NMR.
ISSN:1434-193X
DOI:10.1002/ejoc.200800752