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

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.

SUBMITTER: Lakshman MK

PROVIDER: S-EPMC3735233 | biostudies-literature | 2009 Jan

REPOSITORIES: biostudies-literature

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

Lakshman Mahesh K MK Choudhury Asad A Bae Suyeal S Rochttis Eliezer E Pradhan Padmanava P Kumar Amit A

European journal of organic chemistry 20090101 1

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 th ...[more]

PMID: 23930082

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