Please use this identifier to cite or link to this item:
http://nopr.niscpr.res.in/handle/123456789/16255| Title: | Economical route for oxidative cleavage of double bond to synthesize taxol side chain |
| Authors: | Bhatia, Sumati Singh, Sukhdev Kumar, Rajesh Kumar, Amit Olsen, Carl E Prasad, Ashok K |
| Issue Date: | Mar-2013 |
| Publisher: | NISCAIR-CSIR, India |
| Abstract: | An efficient, economical and industry-friendly methodology has been developed for the synthesis of C-13 side chain of taxol, (2R,3S)-3-benzamido-2-hydroxy-3-phenylpropanoic acid by oxidative cleavage of alkene precursor N-[(1S,2S)-2-(1′-ethoxyethoxy)-1-phenylbut-3-en-1-yl]benzamide using KMnO4-NaIO4-K2CO3 as oxidant in acetone-water in much higher yields of 80% than the conventional RuCl3-NaIO4 method. Further, the developed methodology has been successfully used for the synthesis of O-acetylated taxotere side chain (2R,3S)-2-acetoxy-3-[N-(tert-butoxycarbonyl)amino]-3-phenylpropanoic acid and taxol side chain analogues (2R,3S)- 2-acetoxy-3-(4′′-chloro- / 4′′-fluoro- / 4′′-trifluoromethyl-benzamido)-3-phenylpropanoic acid from their corresponding alkene precursor, which demonstrate the generality of the developed oxidative cleavage methodology. |
| Page(s): | 379-386 |
| ISSN: | 0975-0983(Online); 0376-4699(Print) |
| Appears in Collections: | IJC-B Vol.52B(03) [March 2013] |
Files in This Item:
| File | Description | Size | Format | |
|---|---|---|---|---|
| IJCB 52B(3) 379-386.pdf | 135.24 kB | Adobe PDF | View/Open |
Items in NOPR are protected by copyright, with all rights reserved, unless otherwise indicated.