Bisphosphonate prodrugs. Synthesis and identification of (1-hydroxyethylidene)-1,1-bisphosphonic acid tetraesters by mass spectrometry, NMR spectroscopy and x-ray crystallography

Article abstract of DOI:10.1080/10426500108040589

The preparation and identification of symmetric, H₃CC(OH)[P(O)(OR)₂]₂, where R=Me, Et, Pr¹, Ph, and non-symmetric, H₃CC(OH)[P(O)(OR¹)(OR²)][P(O)(OR³)(O R⁴)], where R¹=Me, R²=R³=R⁴=Ph; R¹=R²=R³=Ph, R⁴=Me; R¹=R³=Me, R²=R⁴=Ph; R¹=R²=Et, Pr¹, Ph and R³=R⁴=Me: tetraester derivatives of etidronate have been studied. Compounds were prepared from HP(O)(OR¹)(OR²) and AcP(O)(OR³)(OR⁴) species under reflux. Mechanism studies have been made using HP(O)(OCD₃)(OPh) and AcP(O)(OMe)(OPh) as starting materials. ¹H, ¹³C, ³¹P NMR data and the MS fragmentation data in the gas phase are reported. The solid-state structures are given for three of the compounds, where R=Et, Ph and R¹=R²=Ph, R³=R⁴=Me.

Full text of DOI:10.1080/10426500108040589

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Phosphorus, Sulfur, and Silicon
and the Related Elements
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BISPHOSPHONATE
PRODRUGS. SYNTHESIS
AND IDENTIFICATION OF (1-
HYDROXYETHYLIDENE)-1,1-
BISPHOSPHONIC ACID
TETRAESTERS BY MASS
SPECTROMETRY, NMR
SPECTROSCOPY AND X-RAY
CRYSTALLOGRAPHY
Petri A. Turhanen a , Markku J. Ahlgren b , Tomi
Järvinen c & Jouko J. Vepsäläinen a
a Univ. Kuopio, Dept. Chem. , P.O. Box 1627,
FIN-70211, Kuopio, Finland
b Univ. Kuopio, Dept. Pharm. Chem. , P.O. Box 1627,
FIN-70211, Kuopio, Finland
c Univ. Joensuu, Dept. Chem. , P.O. Box 111,
FIN-80101, Joensuu, Finland
Published online: 27 Oct 2006.
To cite this article: Petri A. Turhanen , Markku J. Ahlgren , Tomi Järvinen &
Jouko J. Vepsäläinen (2001) BISPHOSPHONATE PRODRUGS. SYNTHESIS AND
IDENTIFICATION OF (1-HYDROXYETHYLIDENE)-1,1-BISPHOSPHONIC ACID TETRAESTERS
BY MASS SPECTROMETRY, NMR SPECTROSCOPY AND X-RAY CRYSTALLOGRAPHY,
Phosphorus, Sulfur, and Silicon and the Related Elements, 170:1, 115-133, DOI:
10.1080/10426500108040589

To link to this article: http://dx.doi.org/10.1080/10426500108040589
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