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1 article(s) from Kukhar, Valery P

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

Vadim D. Romanenko and
Valery P. Kukhar

Beilstein J. Org. Chem. 2013, 9, 991–1001, doi:10.3762/bjoc.9.114

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Scheme 1: Synthesis of hexaethyl dialkylaminomethylidynetrisphosphonates 1 from dichloromethylene dialkylammo...

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Scheme 2: Synthesis and some transformations of trisphosphonate 2.

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Scheme 3: Attempt to synthesize trisphosphonates by the combination of Arbuzov reaction and dialkyl phosphite...

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Scheme 4: Synthesis of hexaethylmethylidynetrisphosphonate 6 via phosphinylation of tetraethyl methylenebisph...

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Scheme 5: Synthetic approach to methylidynetrisphosphonate ester 9.

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Scheme 6: Synthesis of alkylidyne-1,1,1-trisphosphonate esters 12.

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Scheme 7: Two-step one-pot synthesis of propargyl-substituted trisphosphonate 15.

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Scheme 8: Synthetic route to trisphosphonate 18 via 7,7-bisphosphonyl-3,5-di-tert-butylquinone methide 17.

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Scheme 9: Synthesis of trisphosphonate 18 starting from 2,6-di-tert-butyl-4-(dichloromethyl)phenol.

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Scheme 10: Synthesis of triphosphorus derivatives 20 via quinone methides 17 and 19.

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Scheme 11: Unexpected phosphonylation of the aromatic nucleus in reactions of quinone methides 19 and 21.

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Scheme 12: Multistep synthesis of trisphosphonate 18 starting from quinone methide 25.

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Scheme 13: Synthesis of hexaethyl methylidynetrisphosphonate (6) via metal-carbenoid-mediated P–H insertion re...

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Scheme 14: Reaction between tert-butylphosphaethyne and diethyl phosphite in the presence of sodium metal.

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Scheme 15: Cross metathesis of trisphosphonates 12 with 2-methyl-2-butene and the Grubbs second-generation cat...

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Scheme 16: Hydroboration–oxidation of trisphosphonates 12b,e.

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Scheme 17: Reaction of 3-butyn-1-ylidenetrisphosphonate 15 with benzyl azide.

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Scheme 18: The use of the transsilylation reaction for the synthesis of trisphosphonate salts 37.

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Scheme 19: Synthesis of the sodium salt of the acid-labile trisphosphonic acid 38.

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Scheme 20: Acidic hydrolysis of trisphosphonate ester 1a.

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Scheme 21: Methylation of trisphosphonate 1a.

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Scheme 22: Synthesis of the free methylidynetrisphosphonic acid via trisphosphonate salt 38.

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Scheme 23: Synthesis of halomethylidynetrisphosphonate salts 43 and 44 by modified Gross’s procedure.

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Scheme 24: Synthesis of trisphosphonate modified nucleotides. Reagents: i, 5'-O-tosyl adenosine, MeCN; ii, AMP...

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Figure 1: Bond angles and bond distances in pyrophosphate, methylene-1,1-bisphosphonate and fluoromethylidyne...

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Published 24 May 2013

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

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