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

Mahesh K Lakshman; Asad Choudhury; Suyeal Bae; Eliezer Rochttis; Padmanava Pradhan; Amit Kumar

doi:10.1002/ejoc.200800752

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

European J Org Chem. 2009 Jan 1;2009(1):152-159. doi: 10.1002/ejoc.200800752.

Authors

Mahesh K Lakshman¹, Asad Choudhury, Suyeal Bae, Eliezer Rochttis, Padmanava Pradhan, Amit Kumar

Affiliation

¹ Department of Chemistry, The City College and The City University of New York, 160 Convent Avenue, New York, NY 10031-9198, U.S.A.

Abstract

Reactions between secondary amines and phosphorus trichloride (PCl₃) leads to the formation of the corresponding tris(dialkylamino)phosphines or hexaalkylphosphorus triamides [HAPT: (R₂N)₃P]. Reaction of silyl-protected 2'-deoxyinosine and acetyl-protected inosine with the in situ formed HAPT and iodine (I₂) leads to the formation of N⁶,N⁶-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 I₂ has been studied by ³¹P{¹H} NMR.

Keywords: adenosine; amine; inosine; iodine; phosphorus triamide.

Abstract

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