Synthesis of polymerisable phosphodiesters

Details Synthesis of polymerisable phosphodiesters Synthesis of polymerisable phosphodiesters

C - Chemistry, Metallurgy

07

F

C07F 9/141 (2006.01) C07F 9/09 (2006.01) C07F 9/24 (2006.01) C07F 9/54 (2006.01) C07F 9/6561 (2006.01) C07F 9/6571 (2006.01) C07F 9/6574 (2006.01)

Patent

CA 2233161

A mono- or di-functional phosphoramidite phosphitylating agent is used to phosphitylate an ethylenically unsaturated alcohol. The product may be oxidised to form the corresponding phosphate ester which may be reacted in further steps to form phosphoryl choline derivatives. The process is of value in the synthesis of 2-(Methacryloyloxyethyl)-2'- (trimethylammoniumethyl)phosphate, inner salt. It has the advantage over prior art processes in that the starting materials and intermediates are more stable and consequently easier to handle.

On utilise une phosphoramidite mono ou bifonctionnelle comme agent de phosphitylation d'un alcool insaturé en éthylène. Le produit peut être oxydé pour former l'ester de phosphate correspondant qui peut subir d'autres étapes de réaction pour donner des dérivés de la phosphorylcholine. Ce procédé présente un intérêt pour la synthèse du sel interne du 2-(méthacryloyloxyéthyl)-2'-(triméthylammoniuméthyl)phosphate. Il présente par rapport aux techniques antérieures l'avantage d'une plus grande stabilité des produits de départ et des intermédiaires et donc d'une plus grande facilité de manipulation.

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