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Synthesis 2001; 2001(4): 0633-0637
DOI: 10.1055/s-2001-12353
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Bisphosphonate Prodrugs. Selective Synthesis of (1-Hydroxyethylidene)-1,1-bisphosphonate Partial Esters

Petri A. Turhanen* , Markku J. Ahlgren, Tomi Järvinen, Jouko J. Vepsäläinen
  • *University of Kuopio, Department of Chemistry, P. O. Box 1627, 70211, Kuopio, Finland; Fax + 3 58(17)16 32 59; E-mail: Petri.Turhanen@uku.fi
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Publication Date:
31 December 2001 (online)

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Selective methods for the synthesis of (1-hydroxyethylidene)-1,1-bisphosphonate tri-, P,P′-di-, P,P-di- and mono esters have been developed. Preparation is started from selected symmetric or unsymmetric tetraesters of etidronate using alkalimetal salts or trimethylsilyl iodide as dealkylating agents. Synthesis of H3CC(OH)[P(O)(OH)2][P(O)(OH)(OHex)] starting from trimethyl ester of etidronate is also described. 1H, 13C and 31P NMR data are reported including 1 J CP, 2 J CP and 2 J PP couplings. The solid state structure is given for [1-(dimethoxyphosphinyl)-1-hydroxyethyl]-1-phosphonic acid monomethyl ester monopotassium salt (1a).

bisphosphonate - etidronate - partial esters - synthesis - prodrug

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