132201-33-3

Basic information

• Product Name: N-Benzoyl-(2R,3S)-3-phenylisoserine
• Synonyms: N-BENZOYL-(2R,3S)-3-AMINO-2-HYDROXY-3-PHENYL-PROPIONIC ACID;N-BENZOYL-(2R,3S)-3-PHENYLISOSERINE;TAXOL(R) SIDE CHAIN;(2R,3S)-3-Benzoylamino-2-Hydro;(2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropionacid;Taxol side chain alcohol;(2R, 3S)-3-BENZOYLAMINO-2-HYDROXY-3-PHENYLPROPIONACID,98+%;(2R,3S)-3-Benzoylamino-2-hydroxy-3-phenylpropionic acid
• CAS NO: 132201-33-3
• Molecular Formula: C₁₆H₁₅NO₄
• Molecular Weight: 285.29
• EINECS: 1806241-263-5
• Product Categories: Serine Derivatives;Peptide Synthesis;Unnatural Amino Acid Derivatives;Amino Acids & Derivatives;Anti-virals;Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals;Herb extract
• Mol File: 132201-33-3.mol
• Article Data: 29

Chemical Properties

• Melting Point: 169-172 °C(lit.)
• Boiling Point: 580.7 °C at 760 mmHg
• Flash Point: 305 °C
• Appearance: white powder
• Density: 1.316 g/cm³
• Vapor Pressure: 2.51E-14mmHg at 25°C
• Refractive Index: 1.625
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Acetonitrile (Slightly), DMSO (Slightly), Ethanol (Slightly)
• PKA: 3.40±0.17(Predicted)
• CAS DataBase Reference: N-Benzoyl-(2R,3S)-3-phenylisoserine(CAS DataBase Reference)
• NIST Chemistry Reference: N-Benzoyl-(2R,3S)-3-phenylisoserine(132201-33-3)
• EPA Substance Registry System: N-Benzoyl-(2R,3S)-3-phenylisoserine(132201-33-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 132201-33-3(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 132201-33-3 differently. You can refer to the following data:
1. (2R,3S)-N-Benzoyl-3-phenylisoserine is an intermediate in the preparation of potent anticancer drug Paclitaxel (P132500) used to study the location of the binding sites. (2R,3S)-N-Benzoyl-3-phenylisoserine shows cytotoxic, antiviral and immunomodulatory activity.
2. The presence of this chiral side chain has proven to be essential for the biological activity of taxol, one of the most promising anticancer agents being investigated. The challenging synthesis of taxol has stimulated interest in the attachment of the C-13 side chain to naturally derived taxanes like baccatin III.

InChI:InChI=1/C16H15NO4/c18-14(16(20)21)13(11-7-3-1-4-8-11)17-15(19)12-9-5-2-6-10-12/h1-10,13-14,18H,(H,17,19)(H,20,21)/t13-,14+/m0/s1

Upstream product

• 201804-27-5 (2R,3S)-tert-butyl 3-benzamido-2-hydroxy-3-phenylpropanoate 
• 143615-00-3 (2R,3S)-3-amino-3-phenyl-2-hydroxypropionic acid ethyl ester 
• 201804-26-4 (2R,3S)-tert-butyl 3-azido-2-hydroxy-3-phenylpropanoate 
• 158341-43-6 methyl 2-acetoxy-3-azido-3-phenylpropanoate 
• 98-88-4 benzoyl chloride 
• 132201-32-2 (2R,3S)-3-phenylisoserine hydrochloride 
• 136561-53-0 (2R,3S)-2-hydroxy-3-amino-3-phenylpropionic acid 
• 33863-75-1 (±)-cis-phenyloxirane-2-carbonitrile 
• 100-52-7 benzaldehyde 
• 55325-49-0 (±)-anti-3-amino-2-hydroxy-3-phenylpropanamide 
• 32981-85-4 syn-(+/-)-2-hydroxy-3-(benzoylamino)-3-phenylpropanoic acid methyl ester 
• 103150-32-9 (1S,2R)-N-1-(1-phenyl-2,3-dihydroxypropyl)benzamide 
• 5817-02-7 (1S,2S)-2-amino-1-phenyl-1,3-propanediol 
• 10374-29-5 N-benzylidenebenzamide 

Downstream Products

• 32981-85-4 methyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate 
• 33069-62-4 taxol 
• 32981-85-4 syn-(+/-)-2-hydroxy-3-(benzoylamino)-3-phenylpropanoic acid methyl ester 
• 1435475-01-6 (2R,3S)-N-[3-(7-chloroquinolin-4-ylamino)propyl] 2-hydroxy-3-benzamido-3-phenylpropanamide 
• 1435474-92-2 (2R,3S)-[(3R,5aS,6R,8aS,9R,10S,12R,12aR)-decahydro-3,6,9-trimethyl-3,12-epoxy-12H-pyrano[4,3-j]-1,2-benzodioxepin-10-yl] 3-benzamido-2-hydroxy-3-phenylpropanoate 
• 1435474-97-7 (2R,3S)-[2-(7-chloroquinolin-4-ylamino)ethyl] 2-acetoxy-3-benzamido-3-phenylpropanoate 
• 1435474-99-9 (2R,3S)-[3-(7-chloroquinolin-4-ylamino)propyl] 2-acetoxy-3-benzamido-3-phenylpropanoate 
• 1435474-95-5 (2R,3S)-[(((7-chloroquinolin-4-yl)aminoethyl)-1H-1,2,3-triazol-4-yl)methyl]-3-benzamido-2-hydroxy-3-phenylpropanamide 
• 1435475-05-0 (2R,3S)-[(((7-chloroquinolin-4-yl)aminopropyl)-1H-1,2,3-triazol-4-yl)methyl]-3-benzamido-2-hydroxy-3-phenylpropanamide 
• 1435475-06-1 (2R,3S)-[((-3-(7-chloroquinolin-4-yl)aminobenzyl)-1H-1,2,3-triazol-4-yl)methyl]-3-benzamido-2-hydroxy-3-phenylpropanamide 
• 1435475-07-2 (2R,3S)-[((-2-(7-chloroquinolin-4-yl)aminobenzyl)-1H-1,2,3-triazol-4-yl)methyl]-3-benzamido-2-hydroxy-3-phenylpropanamide 
• 1435474-96-6 (2R,3S)-[(3R,5aS,6R,8aS,9R,10S,12R,12aR)-decahydro-3,6,9-trimethyl-3,12-epoxy-12H-pyrano[4,3-j]-1,2-benzodioxepin-10-yl] 2-acetoxy-3-benzamido-3-phenylpropanoate 
• 745076-37-3 (2R,3S)-N-benzoyl-O-acetyl-3-phenylisoserine 
• 1435474-94-4 (2R,3S)-N-benzoylphenylisoserine aminopropyne 

Relevant articles and documents

1,3-Dipolar cycloadditions of carbonyl ylides to aldimines: A three-component approach to syn-α-hydroxy-β-amino esters

(Chemical Equation Presented) A highly diastereoselective Rh II-catalyzed 1,3-dipolar cycloaddition leads to the formation of syn-β-amino alcohols and syn-α-hydroxy-β-amino acids in high yields (see scheme; p-TSA = poro-toluenesulfonic acid, Bn = benzyl). This three-component approach to the addition of metal-associated carbonyl ylides to aldimines was applied to a short enantioselective synthesis of the C13 side chain of taxol.

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

N-benzoyl phenylisoserine derivative as well as synthesis method and application thereof

The invention discloses an N-benzoyl phenylisoserine derivative and a synthesis method thereof. N-benzoyl phenylimine, a diazo compound and isopropyl aldehyde are taken as raw materials, a molecular sieve is taken as a water absorbing agent, rhodium aceta

A convenient one-pot approach to Paclitaxel (Taxol) side chain via 1,3-dipolar cycloaddition of carbonyl ylides and N-benzoylbenzyl imines

An efficient cascade approach to α-hydroxy-β-amino acid derivatives is reported, which goes through a 1,3-dipolar cycloaddition of carbonyl ylides and N-benzoylbenzyl imines and followed by hydrolysis under acidic conditions. This is the first example of using N-benzoylbenzyl imine as dipolarophile for 1,3-dipolar cycloaddition with carbonyl ylide, which provides a direct and convenient access for the one-pot synthesis of paclitaxel side chain and its derivatives.