Synthesis of N 6 , N 6 ‐Dialkyladenine Nucleosides Using Hexaalkylphosphorus Triamides Produced in Situ

Reactions between secondary amines and phosphorus trichloride (PCl 3 ) leads to the formation of the corresponding tris(dialkylamino)phosphanes or hexaalkylphosphorus triamides [HAPTs: (R 2 N) 3 P]. Treatment of silyl‐protected 2′‐deoxyinosine and acetyl‐protected inosine with the HAPTs produced in...

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Published in:European journal of organic chemistry 2009-01, 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)phosphanes or hexaalkylphosphorus triamides [HAPTs: (R 2 N) 3 P]. Treatment of silyl‐protected 2′‐deoxyinosine and acetyl‐protected inosine with the HAPTs produced in situ, together with iodine (I 2 ), leads to the formation of N 6 , N 6 ‐dialkyladenosine and ‐2′‐deoxyadenosine. In some cases the stoichiometry of the amine is important, as is the use of a tertiary amine base. The effect of amine stoichiometry on the reaction between HAPT and I 2 has been studied by 31 P{ 1 H} NMR spectroscopy.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.200800752