(2R,3S)-3-Phenylisoserine

Base Information

• Chemical Name: (2R,3S)-3-Phenylisoserine
• CAS No.: 136561-53-0
• Molecular Formula: C9H11NO3
• Molecular Weight: 181.191
• UNII: FXH8Y63XMR
• Nikkaji Number: J784.784J
• Mol file: 136561-53-0.mol

Synonyms:(2R,3S)-3-Phenylisoserine;136561-53-0;(2R,3S)-3-amino-2-hydroxy-3-phenylpropanoic acid;55325-53-6;Benzenepropanoic acid, b-amino-a-hydroxy-, (aR,bS)-rel-;(2R,3S)-3-azaniumyl-2-hydroxy-3-phenylpropanoate;Benzenepropanoic acid, beta-amino-alpha-hydroxy-, (alphaR,betaS)-;(2r,3s)-phenylisoserine;FXH8Y63XMR;3-(2R,3S)-Phenylisoserine;SCHEMBL487425;(2R,3S)-3-Phenyl-Isoserine;(2R, 3S)-3-Phenyl-Isoserine;3-Phenylisoserine, (2R,3S)-;RZARFIRJROUVLM-JGVFFNPUSA-N;AMY21980;MFCD00671670;AKOS006274499;AC-25882;CS-0269707;EN300-258810;F12982;(2R,3S)-3-amino-3-phenyl-2-hydroxypropionic acid;(alphaR,betaS)-beta-Amino-alpha-hydroxybenzenepropanoic acid;Benzenepropanoic acid, beta-amino-alpha-hydroxy-, [R-(R*,S*)]-

Chemical Property of (2R,3S)-3-Phenylisoserine

Chemical Property:

• Vapor Pressure: 7.87E-06mmHg at 25°C
• Refractive Index: 1.593
• Boiling Point: 360.6 °C at 760 mmHg
• PKA: 2.56±0.27(Predicted)
• Flash Point: 171.9 °C
• PSA: 83.55000
• Density: 1.206 g/cm³
• LogP: 0.83220
• Storage Temp.: 2-8°C
• XLogP3: -2.5
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 181.07389321
• Heavy Atom Count: 13
• Complexity: 178

Purity/Quality:

98%,99%, ^*data from raw suppliers

(2R,3S)-3-Phenylisoserine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C(C(C(=O)O)O)N
• Isomeric SMILES: C1=CC=C(C=C1)[C@@H]([C@H](C(=O)O)O)N
• Uses: Intermediate for the synthesis of taxol.

Technology Process of (2R,3S)-3-Phenylisoserine

There total 42 articles about (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: 100.0%

(3R,4S)-3-hydroxy-4-phenylazetidin-2-one (132127-34-5) → (2R,3S)-2-hydroxy-3-amino-3-phenylpropionic acid (136561-53-0)

Guidance literature:

With hydrogenchloride; In water;

DOI:10.1002/1521-3773(20020301)41:5<831::AID-ANIE831>3.0.CO;2-6

Reference yield: 97.0%

(2R,3S)-3-amino-2-benzyloxy-3-phenylpropanoic acid → (2R,3S)-2-hydroxy-3-amino-3-phenylpropionic acid (136561-53-0)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; at 40 ℃; under 37503.8 Torr; Flow reactor;

DOI:10.1016/j.molcatb.2015.11.011

Reference yield: 92.0%

(2R,3S) 2-hydroxy-3-amino-3-phenylpropionamide (141901-21-5) → (2R,3S)-2-hydroxy-3-amino-3-phenylpropionic acid (136561-53-0)

Guidance literature:

With barium dihydroxide; In water; for 8h; Heating;

DOI:10.1021/jo00041a054

upstream raw materials:

2-chloro-3-hydroxy-3-phenyl-propionic acid

2-hydroxy-3-amino-3-phenylpropionamide

(2RS,3SR)-2,3-epoxy-3-phenyl-propionic acid

(±)-anti-3-amino-2-hydroxy-3-phenylpropanamide

Downstream raw materials:

benzaldehyde

2-hydroxy-3-(4-methyl benzenesulfonylamino)-3-phenyl-propionic acid methyl ester

(2R,3S)-methyl 3-acetamido-2-acetyloxy-3-phenylpropanoate

Methyl N-acetyl-3-phenylisoserine

Refernces

• 1、 Galla, Zsolt,Beke, Ferenc,Forró, Eniko,Fül?p, Ferenc. "Enantioselective hydrolysis of 3,4-disubstituted β-lactams. An efficient enzymatic method for the preparation of a key Taxol side-chain intermediate". . p. 107 - 112. Retrieved 2015/12/01.
• 2、 Wilding, Birgit,Veselá, Alicja B.,Perry, Justin J. B.,Black, Gary W.,Zhang, Meng,Martínková, Ludmila,Klempier, Norbert. "An investigation of nitrile transforming enzymes in the chemo-enzymatic synthesis of the taxol sidechain". . p. 7803 - 7812. Retrieved 2015/07/15.