N-Benzoyl-(2R,3S)-3-phenylisoserine

Base Information

• Chemical Name: N-Benzoyl-(2R,3S)-3-phenylisoserine
• CAS No.: 132201-33-3
• Molecular Formula: C16H15NO4
• Molecular Weight: 285.299
• Hs Code.: 29242990
• European Community (EC) Number: 631-348-7
• UNII: D998Q2WJCM
• DSSTox Substance ID: DTXSID10157433
• Nikkaji Number: J391.951J
• Wikidata: Q27276267
• ChEMBL ID: CHEMBL134943
• Mol file: 132201-33-3.mol

Synonyms:132201-33-3;N-Benzoyl-(2R,3S)-3-phenylisoserine;(2R,3S)-3-benzamido-2-hydroxy-3-phenylpropanoic acid;(2R,3S)-N-Benzoyl-3-phenylisoserine;(2R,3S)-N-Benzoyl-3-phenyl Isoserine;N-Benzoyl-3-phenylisoserine, (2R,3S)-;UNII-D998Q2WJCM;D998Q2WJCM;N-BENZOYL-(2R,3S)-3-AMINO-2-HYDROXY-3-PHENYL-PROPIONIC ACID;Benzenepropanoic acid, beta-(benzoylamino)-alpha-hydroxy-, (alphaR,betaS)-;188003-77-2;MFCD00274633;(2R,3S)-3-(Benzoylamino)-2-hydroxy-3-phenylpropanoic Acid ((2R,3S)-N-Benzoyl-3-phenylisoserine);taxol side chain;SCHEMBL6277;CHEMBL134943;(2R,3S)-3-Benzoylamino-2-hydroxy-3-phenyl-propionic acid;DTXSID10157433;HYJVYOWKYPNSTK-UONOGXRCSA-N;(2R,3S)-N-Benzoylphenylisoserine;AMY16032;BCP22946;HY-N2380;s9395;AKOS015917754;AC-9033;BCP9000974;CCG-267321;N-benzoyl-(2R,3S)-3-phenyl-isoserine;N-Benzoyl-(2R,3S,)-3-phenylisoserine;AS-13810;BP-22968;BCP0726000152;CS-0022559;N-Benzoyl-(2R,3S)-3-phenylisoserine, 98%;F14253;J-006139;Q27276267;(2R,3S)-3-(benzamido)-2-hydroxy-3-phenylpropanoic acid;(2R,3S)-rel-3-Benzamido-2-hydroxy-3-phenylpropanoic acid;(2R,3S)-rel-3-Benzamido-2-hydroxy-3-phenylpropanoicacid;N-Benzoyl-(2R,3S)-3-amino-2-hydroxy-3-phenylpropanoic acid;(2R,3S)-3-BENZOYLAMINO-2-HYDROXY-3-PHENYLPROPIONIC ACID;BENZENEPROPANOIC ACID, .BETA.-(BENZOYLAMINO)-.ALPHA.-HYDROXY-, (.ALPHA.R,.BETA.S)-

Chemical Property of N-Benzoyl-(2R,3S)-3-phenylisoserine

Chemical Property:

• Appearance/Colour: white powder
• Vapor Pressure: 2.51E-14mmHg at 25°C
• Melting Point: 169-172 °C(lit.)
• Refractive Index: 1.625
• Boiling Point: 580.7 °C at 760 mmHg
• PKA: 3.40±0.17(Predicted)
• Flash Point: 305 °C
• PSA: 86.63000
• Density: 1.316 g/cm³
• LogP: 1.99410
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Acetonitrile (Slightly), DMSO (Slightly), Ethanol (Slightly)
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 285.10010796
• Heavy Atom Count: 21
• Complexity: 359

Purity/Quality:

99% ^*data from raw suppliers

(2R,3S)-N-Benzoyl-3-phenylIsoserine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C(C(C(=O)O)O)NC(=O)C2=CC=CC=C2
• Isomeric SMILES: C1=CC=C(C=C1)[C@@H]([C@H](C(=O)O)O)NC(=O)C2=CC=CC=C2
• Uses: (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. 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.

Technology Process of N-Benzoyl-(2R,3S)-3-phenylisoserine

There total 76 articles about N-Benzoyl-(2R,3S)-3-phenylisoserine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 89.0%

ethyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate (153433-80-8) → (2R,3S)-N-benzoyl-3-phenylisoserine (132201-33-3)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; methanol; water; at 20 ℃; for 1h;

DOI:10.1002/anie.200500296 DOI:10.1002/adsc.200600324

Reference yield: 86.3%

(±)-syn-3-amino-2-benzyloxy-3-phenylpropanoic acid → N-benzoyl-(2R*,3S*)-3-phenylisoserine (7309-55-9,7309-56-0,54323-80-7,94299-20-4,132201-33-3)

Guidance literature:

(±)-syn-3-amino-2-benzyloxy-3-phenylpropanoic acid; In methanol; aq. phosphate buffer; at 20 - 40 ℃; pH=8;

With hydrogenchloride; In water;

DOI:10.1039/c5ob01191d

Reference yield: 80.0%

methyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate (32981-85-4) → (2R,3S)-N-benzoyl-3-phenylisoserine (132201-33-3)

Guidance literature:

With potassium carbonate; In methanol; at 23 ℃; for 12h;

DOI:10.1021/jo00057a054

upstream raw materials:

(2R,3S)-2-hydroxy-3-amino-3-phenylpropionic acid

benzoyl chloride

(2R,3S)-3-phenylisoserine hydrochloride

methyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate

Downstream raw materials:

(2R,3S)-N-[2-(7-chloroquinolin-4-ylamino)ethyl]-2-hydroxy-3-benzamido-3-phenylpropanamide

(2R,3S)-[3-(7-chloroquinolin-4-ylamino)propyl] 3-benzamido-2-hydroxy-3-phenylpropanoate

(2R,3S)-[2-(7-chloroquinolin-4-ylamino)ethyl] 3-benzamido-2-hydroxy-3-phenylpropanoate

(2R,3S)-N-benzoylphenylisoserine aminopropyne

Refernces

• 1、 Richheimer, Steven L.,Tinnermeier, David M.,Timmons, Daniel W.. "High-performance liquid chromatographic assay of taxol". . p. 2323 - 2326. Retrieved 1992.
• 2、 Matsushima, Yoshitaka,Orita, Mina. "Concise synthesis of the Taxol side chain and demethoxy-4-epi-cytoxazone via oxazoline formation through intramolecular benzylic substitution of a bis-trichloroacetimidate". supporting information. . Retrieved 2021/05/10.
• 3、 Sheng, Jiajun,Chang, Huan,Qian, Yu,Ma, Mingliang,Hu, Wenhao. "A convenient one-pot approach to Paclitaxel (Taxol) side chain via 1,3-dipolar cycloaddition of carbonyl ylides and N-benzoylbenzyl imines". supporting information. p. 2141 - 2144. Retrieved 2018/05/05.