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Synthesis of functionalized alkoxyalkylidene gem-bisphosphonates

Jean-Pierre Haelters 1 Hélène Couthon 1 Alan Le Goff 1 Gaelle Simon 1 Bernard Corbel 1 Paul-Alain Jaffres 1
1 CEMCA - Chimie, Electrochimie Moléculaires et Chimie Analytique
Abstract : We report the synthesis of a series of new functionalized bisphosphonates and bisphosphonic acids with an alkoxy group fixed at the geminal carbon, which is proposed to increase their lipophilicity and so their bioavailability. Subsequently, the alkylation of these alkoxy bisphosphonates with allyl bromide is reported. The reactivity of the allyl group has been studied to give access to alkoxy bisphosphonates functionalized by diverse groups including alcohol, aldehyde, carboxylic acid, epoxide and amine.
Keywords : Bisphosphonates Bisphosphonic acids Aminobisphosphonates Alkoxy methylene bisphosphonates
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https://hal.univ-brest.fr/hal-01580463
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Submitted on : Friday, September 1, 2017 - 3:30:01 PM
Last modification on : Thursday, November 12, 2020 - 12:04:02 PM

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Jean-Pierre Haelters, Hélène Couthon, Alan Le Goff, Gaelle Simon, Bernard Corbel, et al.. Synthesis of functionalized alkoxyalkylidene gem-bisphosphonates. Tetrahedron, Elsevier, 2008, 64 (27), pp.6537 - 6543. ⟨10.1016/j.tet.2008.04.052⟩. ⟨hal-01580463⟩

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