(2R,3S)-3-Phenylisoserine methyl ester

Base Information

• Chemical Name: (2R,3S)-3-Phenylisoserine methyl ester
• CAS No.: 131968-74-6
• Molecular Formula: C₁₀H₁₃NO₃
• Molecular Weight: 195.218
• Hs Code.: 2922509090
• European Community (EC) Number: 881-457-0
• DSSTox Substance ID: DTXSID50436431
• Nikkaji Number: J1.859.026C
• Mol file: 131968-74-6.mol

Synonyms:(2R,3S)-3-Phenylisoserine methyl ester;131968-74-6;methyl (2R,3S)-3-amino-2-hydroxy-3-phenylpropanoate;157240-36-3;(2R,3S)-Methyl 3-amino-2-hydroxy-3-phenylpropanoate;SCHEMBL487429;DTXSID50436431;WZPZWAQKLOPJEL-DTWKUNHWSA-N;AMY21982;MFCD09837612;AKOS006327901;AKOS015850893;GS-4520;AC-25883;(2R,3S)-beta-phenyl isoserine methyl ester;(2R,3S)-beta-phenyl-isoserine methyl ester;CS-0022558;EN300-1069848;J-500984;(2R,3S)-Methyl3-amino-2-hydroxy-3-phenylpropanoate;rel-Methyl (2R,3S)-3-amino-2-hydroxy-3-phenylpropanoate;(2R,3S)-2-Hydroxy-3-amino-3-phenylpropionic acid methyl ester;Benzenepropanoic acid,b-amino-a-hydroxy-,methyl ester,(ar,bs)-rel-;Benzenepropanoic acid, beta-amino-alpha-hydroxy-, methyl ester, (alphaR,betaS)-rel-

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

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 87-88℃
• Refractive Index: 1.557
• Boiling Point: 343.025 °C at 760 mmHg
• PKA: 10.35±0.45(Predicted)
• Flash Point: 161.256 °C
• PSA: 72.55000
• Density: 1.212 g/cm³
• LogP: 0.92060
• Storage Temp.: 2-8°C
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 195.08954328
• Heavy Atom Count: 14
• Complexity: 190

Purity/Quality:

99% ^*data from raw suppliers

(2R,3S)-3-Phenylisoserine methyl ester 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C(C(C1=CC=CC=C1)N)O
• Isomeric SMILES: COC(=O)[C@@H]([C@H](C1=CC=CC=C1)N)O

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

There total 5 articles about (2R,3S)-3-Phenylisoserine methyl ester 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: 95.0%

Methyl (2S*,3S*)-2-hydroxy-3-azido-3-phenyl-propionate → methyl (2R*,3R*)-3-phenyl-3-amino-2-hydroxypropanoate (131968-74-6,140408-28-2,150949-07-8)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; for 1h;

DOI:10.1002/recl.19921110202

Reference yield: 80.0%

methanol (67-56-1) + Chloro-acetic acid (3S,4R)-2-oxo-4-phenyl-azetidin-3-yl ester (131968-72-4) → (2R,3S)-3-Amino-2-hydroxy-3-phenyl-propionic acid methyl ester (131968-74-6,140408-28-2,150949-07-8)

Guidance literature:

With chloro-trimethyl-silane;

DOI:10.1016/S0040-4039(00)97083-7

Reference yield:

1-(4-methoxyphenyl)-4-phenylazetidine-2,3-dione (94612-33-6,112383-85-4) → (2R,3S)-3-Amino-2-hydroxy-3-phenyl-propionic acid methyl ester (131968-74-6,140408-28-2,150949-07-8)

Guidance literature:

Multi-step reaction with 4 steps

1: NaBH₄ / methanol; tetrahydrofuran

2: pyridine / CH₂Cl₂

3: (NH₄)2Ce(NO₃)6 / acetonitrile; H₂O / 0.75 h / 0 - 5 °C

4: 80 percent / ClSiMe₃

With pyridine; sodium tetrahydroborate; chloro-trimethyl-silane; ammonium cerium(IV) nitrate; In tetrahydrofuran; methanol; dichloromethane; water; acetonitrile;

DOI:10.1016/S0040-4039(00)97083-7

upstream raw materials:

methanol

Chloro-acetic acid (3S,4R)-2-oxo-4-phenyl-azetidin-3-yl ester

1-(4-methoxyphenyl)-4-phenylazetidine-2,3-dione

(+/-)-(3R,4S)-3-hydroxy-4-phenyl-N-(4-methoxyphenyl)azetidin-2-one

Downstream raw materials:

syn-(+/-)-2-hydroxy-3-(benzoylamino)-3-phenylpropanoic acid methyl ester

Refernces

• 1、 Palomo,Arrieta,Cossio,Aizpurua,Mielgo,Aurrekoetxea. "Highly stereoselective synthesis of α-hydroxy β-amino acids through β-lactams: Application to the synthesis of the taxol and bestatin side chains and related systems". . p. 6429 - 6432. Retrieved 2007/10/02.