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Synthesis of Unsymmetrical Difluoromethylene Bisphosphonates.

ABSTRACT: We demonstrate the use of the symmetrical diethyl(dimethyl)difluoromethylene bisphosphonate reagent for the synthesis of terminal and unsymmetrical difluoromethylene bisphosphonates, close analogues of biologically important molecules. The difference in reactivity of the methyl and ethyl groups in the symmetrical diethyl(dimthyl)difluoromethylene bisphosphonate is exploited in a stepwise demethylation-condensation sequence to functionalize either side of the reagent to allow the generation of a series of close bioisosteres of natural pyrophosphate molecules, including ADPr, CDP-glycerol and CDP-ribitol.

SUBMITTER: Guo J

PROVIDER: S-EPMC10825822 | biostudies-literature | 2024 Jan

REPOSITORIES: biostudies-literature

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Synthesis of Unsymmetrical Difluoromethylene Bisphosphonates.

Guo Jianyun J Balić Pascal P Borodkin Vladimir S VS Filippov Dmitri V DV Codée Jeroen D C JDC

Organic letters 20240112 3

We demonstrate the use of the symmetrical diethyl(dimethyl)difluoromethylene bisphosphonate reagent for the synthesis of terminal and unsymmetrical difluoromethylene bisphosphonates, close analogues of biologically important molecules. The difference in reactivity of the methyl and ethyl groups in the symmetrical diethyl(dimthyl)difluoromethylene bisphosphonate is exploited in a stepwise demethylation-condensation sequence to functionalize either side of the reagent to allow the generation of a ...[more]

PMID: 38215221

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