Stereoselective preparation of .beta.-phenylisoserine and...

Details Stereoselective preparation of .beta.-phenylisoserine and... Stereoselective preparation of .beta.-phenylisoserine and...

C - Chemistry, Metallurgy

07

D

C07D 305/14 (2006.01) C07C 271/10 (2006.01) C07C 271/22 (2006.01) C07D 405/12 (2006.01) C07D 407/12 (2006.01) C07D 413/12 (2006.01) C07F 7/10 (2006.01)

Patent

CA 2146374

Method of stereoselective preparation of a derivative of (beta)-phenylisoserine of formula (I) by the action of an N-carbonylbenzylimine of formula (II) on an optically active amide of a protected hydroxyacetic acid of formula (III), followed by hydrolysis of the product obtained. In formulae (I), (II) or (III), R is an optionally substituted phenyl radical or R1-O, Ar is an optionally substituted aryl radical and G1 is a hydroxy function protection grouping. The product of formula (I) is particularly useful in preparing taxol and Taxotere which have remarkable antitumor properties.

Procédé de préparation stéréosélective d'un dérivé de la .beta.-phénylisosérine de formule (I) par action d'une N-carbonylben- zylimine de formule (II) sur un amide optiquement actif d'un acide hydroxyacétique protégé de formule (III), suivie de l'hydro- lyse du produit obtenu. Dans les formules (I), (II) ou (III), R représente un radical phényle eventuellement substitué ou R1-O, Ar représente un radical aryle éventuellement substitué et G1 représente un groupement protecteur de la fonction hydroxy. Le produit de formule (I) est particulièrement utile pour la préparation du taxol et du Taxotère qui présentent des propriétés antitumorales remarquables.

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