Literature DB >> 21916407

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

Jacqueline P Smits1, David F Wiemer.   

Abstract

The α-trisphosphonic acid esters provide a unique spatial arrangement of three pan class="Chemical">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 the reactivity of these new compounds has been studied in representative reactions that afford additional examples of this functionality.

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Year:  2011        PMID: 21916407      PMCID: PMC3967447          DOI: 10.1021/jo201523w

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  17 in total

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4.  Fluorescently labeled risedronate and related analogues: "magic linker" synthesis.

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5.  Fragmentation of carbonyl oxides by N-oxides: an improved approach to alkene ozonolysis.

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6.  Facile dephosphonylation of beta-ketophosphonic acids: mechanistic studies.

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Journal:  Org Lett       Date:  2006-08-03       Impact factor: 6.005

7.  Alpha-phosphono lactone analogues of cytidine and cytosine arabinoside diphosphates: synthesis via ring closing metathesis.

Authors:  Xuemei Chen; David F Wiemer
Journal:  J Org Chem       Date:  2003-08-22       Impact factor: 4.354

8.  Synthesis and biological activity of isoprenoid bisphosphonates.

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9.  Mono- and dialkyl isoprenoid bisphosphonates as geranylgeranyl diphosphate synthase inhibitors.

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Journal:  Bioorg Med Chem       Date:  2007-09-18       Impact factor: 3.641

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  4 in total

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2.  Methylidynetrisphosphonates: Promising C1 building block for the design of phosphate mimetics.

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Journal:  Beilstein J Org Chem       Date:  2013-05-24       Impact factor: 2.883

3.  Synthesis of isoprenoid bisphosphonate ethers through C-P bond formations: Potential inhibitors of geranylgeranyl diphosphate synthase.

Authors:  Xiang Zhou; Jacqueline E Reilly; Kathleen A Loerch; Raymond J Hohl; David F Wiemer
Journal:  Beilstein J Org Chem       Date:  2014-07-18       Impact factor: 2.883

Review 4.  Phosphonic acid: preparation and applications.

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  4 in total

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