Synthesis And Technology Of Taxol C-13 Side Chain

Taxol which was extracted taxus brevifolia bark is a diterpenoid. It has a very good effect on ovarian cancer and many cancers. Now it was obtained through the semi-synthetic method that is connection of C-13 side chain with 10-deacetylbaccatin III.Therefore, synthesis and technology of taxol C-13 side chain is great practical valuable.The C-13 side chain synthetic route was study in this paper.The best synthetic route was determined through comparing with the various methods. Started from chloroacetyl chloride and chiral menthol, chloroacetic acid ester was obtained, and then cyclized to obtain (1S,2R.5S)-(+)-Menthyl(2R,3R)-3-phenylglycidate by Darzen condensation with benzaldeh-yde. After the azide of the former product, it was then reduced. Finally, C-13 side chain of taxol was obtained after hydrolysis reaction. This synthetic route was quite feasible because of common raw materials and mild reaction conditions. Besides,each intermediate was solid and was convenient to purified and dealt with, which is beneficial to industrial production.Single factor experiments were carried to determine the most effective conditions such as reaction time, temperature, material ratio and catalyzer dose. A few steps were carried out to determine schemes that meet different requirments. Products werecharacterized by the melting point determination, mass(MS),1H nuclear magnetic resonance(HNMR), the results showed that they are in line with the target products.The rourte of synthesis of C-13 side chain of taxol was verified to be efficient.