C - Chemistry – Metallurgy – 07 – D
Patent
C - Chemistry, Metallurgy
07
D
C07D 305/14 (2006.01)
Patent
CA 2444693
9-dihydro-13-acetylbaccatin III, one of the chemicals obtained from Taxus canadensis is used to produce, inter alia, 10-deacetylbaccatin III, a useful intermediate for the preparation of paclitaxel and analogues thereof. The 9-dihydro-13- acetylbaccatin III is converted into the 10-deacetylbaccatin III by a simple three-step process involving (a)replacement of the C-7 hydroxyl group of the 9-dihydro compound with a protecting group, (b)the oxidizing of the C-7 protected compound to produce a C-9 ketone, and (c)the deprotecting of the C-9 ketone to produce 10- deacetylbaccatin III.
La 9-dihydro-13-acétylbaccatine III, un des produits chimiques obtenus à partir de Taxus canadensis, est utilisée pour produire, entre autres, de la 10-désacétylbaccatine III, un intermédiaire utile pour la préparation de paclitaxel et de ses analogues. La 9-dihydro-13-acétylbaccatine III est convertie en 10-désacétylbaccatine III grâce à un procédé simple en trois étapes, comportant a) le remplacement du groupement hydroxyle en C7 du composé 9-dihydro par un groupement protecteur, b) l'oxydation du composé en C7 protégé, afin d'obtenir une cétone en C9, et c) la déprotection de la cétone en C9 afin d'obtenir la 10-désacétylbaccatine III.
Deslongchamps Ghislain
Findlay John
Li Guoqiang
Fogler Rubinoff Llp
University Of New Brunswick
LandOfFree
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