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Synthesis and reactivity of alkyl-1,1,1-trisphosphonate esters.

ABSTRACT: The ?-trisphosphonic acid esters provide a unique spatial arrangement of three phosphonate groups and may represent an attractive motif for inhibitors of enzymes that utilize di- or triphosphate substrates. To advance studies of this unique functionality, a general route to alkyl derivatives of the parent system (R = H) has been developed. A set of new ?-alkyl-1,1,1-trisphosphonate esters has been prepared through phosphinylation and subsequent oxidation of tetraethyl alkylbisphosphonates, and the reactivity of these new compounds has been studied in representative reactions that afford additional examples of this functionality.

SUBMITTER: Smits JP

PROVIDER: S-EPMC3967447 | biostudies-literature | 2011 Nov

REPOSITORIES: biostudies-literature

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Synthesis and reactivity of alkyl-1,1,1-trisphosphonate esters.

Smits Jacqueline P JP Wiemer David F DF

The Journal of organic chemistry 20111004 21

The α-trisphosphonic acid esters provide a unique spatial arrangement of three phosphonate groups and may represent an attractive motif for inhibitors of enzymes that utilize di- or triphosphate substrates. To advance studies of this unique functionality, a general route to alkyl derivatives of the parent system (R = H) has been developed. A set of new α-alkyl-1,1,1-trisphosphonate esters has been prepared through phosphinylation and subsequent oxidation of tetraethyl alkylbisphosphonates, and t ...[more]

PMID: 21916407

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