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- Title
Combined Phosphoramidite-Phosphodiester Reagents for the Synthesis of Methylene Bisphosphonates.
- Authors
Engelsma, Sander B.; Meeuwenoord, Nico J.; Overkleeft, Hermen S.; van der Marel, Gijsbert A.; Filippov, Dmitri V.
- Abstract
A new class of phosphanylmethylphosphonate reagents has been developed to enable the controlled synthesis of methylene bisphosphonate mono- and diesters. Condensation of such reagents with an alcohol of choice through azole-mediated phosphoramidite chemistry followed by in situ oxidation provides orthogonally protected methylene bisphosphonate tetraesters. Global deprotection of the tetraester leads to terminal methylene bisphosphonates. Alternatively, selective deprotection at the terminal phosphonate followed by a condensation between the acquired methylene bisphosphonate triester and a second alcohol leads to methylene bisphosphonates diesters.
- Subjects
PHOSPHORAMIDITES; PHOSPHODIESTERS; METHYLENE group; DIPHOSPHONATES; CHEMICAL reagents; CHEMICAL synthesis
- Publication
Angewandte Chemie International Edition, 2017, Vol 56, Issue 11, p2955
- ISSN
1433-7851
- Publication type
Article
- DOI
10.1002/anie.201611878