949023-16-9

Basic information

• Product Name: (4S,5R)-3-Benzoyl-2-(4-methoxyphenyl)-4-phenyl-5-oxazolidinecarboxylic acid
• Synonyms: (4S,5R)-3-Benzoyl-2-(4-methoxyphenyl)-4-phenyl-5-oxazolidinecarboxylic acid;Paclitaxel side chain acid;(4S,5R)-2-(4-methoxyphenyl)-N-benzoyl-4-phenyloxazolidine-5-carboxylic acid;3-{[2-(4-Methoxyphenyl)phenyl]carbonyl}-4-phenyl-1,3-oxazolidine-5-carboxylic acid;(4S,5R)-3-benzoyl-2-(4-anisyl)-4-phenyl-5-oxazolidinecarboxylic acid;(4S,5R)-3-Benzoyl-2-(4-Methoxyphenyl)-4-phenyloxazolidine-5-carboxylic acid;(4S,5R)-3-benzoyl-2-(4-anisyl)-4-phenyl-5-oxazolidinecarboxylic;5-Oxazolidinecarboxylicacid, 3-benzoyl-2-(4-Methoxyphenyl)-4-phenyl-, (4S,5R)-
• CAS NO: 949023-16-9
• Molecular Formula: C24H21NO5
• Molecular Weight: 403.43
• EINECS: 1592732-453-0
• Product Categories: Plant extracts;Herb extract
• Mol File: 949023-16-9.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 642.269 °C at 760 mmHg
• Flash Point: 342.232 °C
• Appearance: /
• Density: 1.291
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.624
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 2.85±0.60(Predicted)
• CAS DataBase Reference: (4S,5R)-3-Benzoyl-2-(4-methoxyphenyl)-4-phenyl-5-oxazolidinecarboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (4S,5R)-3-Benzoyl-2-(4-methoxyphenyl)-4-phenyl-5-oxazolidinecarboxylic acid(949023-16-9)
• EPA Substance Registry System: (4S,5R)-3-Benzoyl-2-(4-methoxyphenyl)-4-phenyl-5-oxazolidinecarboxylic acid(949023-16-9)

Safety Data

• Hazardous Substances Data: 949023-16-9(Hazardous Substances Data)

Usage

Uses

Modification of (4S,5R)-3-Benzoyl-2-(4-methoxyphenyl)-4-phenyloxazolidine-5-carboxylic Acid which has similar potent cytotoxic activities in MCF-7 human tumor cell line as paclitaxel.

InChI:InChI=1/C24H21NO5/c1-29-19-14-12-18(13-15-19)23-25(22(26)17-10-6-3-7-11-17)20(21(30-23)24(27)28)16-8-4-2-5-9-16/h2-15,20-21,23H,1H3,(H,27,28)/t20-,21+,23?/m0/s1

Upstream product

• 32981-85-4 methyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate 
• 129320-33-8 5-Ethyl (2R,3R)-2-benzyloxy-3-hydroxy-3-phenylpropanethioate 
• 202390-82-7 5-Ethyl (2R,3S)-3-amino-2-benzyloxy-3-phenylpropanethioate 
• 222727-06-2 S-Ethyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanethioate 
• 202390-83-8 5-Ethyl (2R,3S)-3-benzoylamino-2-benzyloxy-3-phenylpropanethioate 
• 442850-34-2 (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoic acid benzyl ester 
• 157240-36-3 (2R,3S)-3-phenylisoserine methyl ester 
• 132201-32-2 (2R,3S)-3-phenylisoserine hydrochloride 
• 136561-53-0 (2R,3S)-2-hydroxy-3-amino-3-phenylpropionic acid 
• 98-88-4 benzoyl chloride 
• 132201-33-3 (2R,3S)-N-benzoyl-3-phenylisoserine 
• 196929-85-8 (R)-N-benzylidene-2-methylpropane-2-sulfinamide 
• 911199-15-0 C₂₅H₃₃NO₆S 
• 1531632-31-1 benzyl (4S,5R)-3-benzoyl-2-(4-methoxyphenyl)-4-phenyl-5-oxazolidine carboxylate 

Relevant articles and documents

Synthetic method of paclitaxel side chain

The invention discloses a synthetic method of a paclitaxel side chain. The method comprises the steps of taking (2R, 3S)-3-phenyl isoserine hydrochloride as a raw material; carrying out esterificationreaction under the participation of methanol and thionyl chloride to obtain (2R, 3S)-phenyl isoserine methyl ester; then preparing (2R, 3S)-N-benzoyl-phenyl isoserine methyl ester through a benzoylation reaction; preparing (4S, 5R)-5-methoxycarbonyl-2-(4-methoxyphenyl)-4-phenyl-3-benzoyl-1,3-oxazolidine through a cyclization protection reaction; finally, obtaining a paclitaxel side chain crude product through hydrolysis, and further purifying the paclitaxel side chain crude product through recrystallization to obtain a paclitaxel side chain finished product. The method is simple and easy to operate, short in production period, low in cost, high in purification efficiency and suitable for industrial application and market popularization.

Synthesis and biological activity of C-7, C-9 and C-10 modified taxane analogues from 1-deoxybaccatin VI

A series of C-7, C-9 and C-10 modified taxane analogues were synthesized and their in vitro anticancer activities against three human cancer cell lines: A-549 (human lung cancer cell line), MDA-MB-231 (human breast cancer cell line), A-549/T (human lung c

The synthesis of novel taxoids for oral administration

A group of novel taxoids, with modifications at C-7, C-10, C-3′ and C-14 positions of paclitaxel, was synthesized in order to improve their biological profile by decreasing their affinity with P-glycoprotein (P-gp) and increasing cellular permeability. Most of the new taxoids demonstrated the similar potent cytotoxic activities in MCF-7 human tumor cell line as paclitaxel in vitro. In the permeability assay with monolayers of Caco-2 cells, most of the compounds demonstrated an increased trans-cellular transport in A-to-B direction in comparison with paclitaxel. Among them the compounds T-13, T-15 and T-26 showed the highest permeability, and with efflux ratios better than that of ortataxel. The interaction of the compounds T-13 and T-26 with P-gp was evaluated using Madin-Darby canine kidney (MDCK)-multidrug resistance-1(MDR1) and MDCK-wild-type (WT). The results indicated that T-13 and T-26 were poor substrates for P-gp and possessed inhibiting effects of P-gp mediated efflux. It was thus clear that simultaneous modifications at the C-7, C-10 and C-3′ positions of paclitaxel significantly impaired its interactions with P-gp and interfered with P-gp mediated efflux.