Methyl (2r,3s)-3-(benzoylamino)-2-hydroxy-3-phenylpropanoate

Base Information

• Chemical Name: Methyl (2r,3s)-3-(benzoylamino)-2-hydroxy-3-phenylpropanoate
• CAS No.: 32981-85-4
• Molecular Formula: C17H17NO4
• Molecular Weight: 299.326
• Hs Code.: 2924299090
• European Community (EC) Number: 608-809-6
• DSSTox Substance ID: DTXSID20865658
• Nikkaji Number: J1.826.437D
• Mol file: 32981-85-4.mol

Synonyms:32981-85-4;methyl (2r,3s)-3-(benzoylamino)-2-hydroxy-3-phenylpropanoate;methyl 3-benzamido-2-hydroxy-3-phenylpropanoate;methyl (2R,3S)-3-benzamido-2-hydroxy-3-phenylpropanoate;Methyl(2r,3s)-n-benzoyl-3-phenylisoserine;132074-01-2;C-13 side chain for paclitaxel II;SCHEMBL1071825;DTXSID20865658;UYJLJICUXJPKTB-UHFFFAOYSA-N;AKOS025401492;N-Benzoyl-betaphenyl isoserine methyl ester;N-Benzoyl-beta-phenyl isoserine methyl ester;2R,3S)-N-tert-butoxycarbony-3-phenylisoserine methyl ester;alpha-Hydroxy-beta-(benzoylamino)benzenepropionic acid methyl ester;N-Benzoyl-(2R,3S)-3-Amino-2-hydroxy-3-phenyl-propionic acid methyl ester

Chemical Property of Methyl (2r,3s)-3-(benzoylamino)-2-hydroxy-3-phenylpropanoate

Chemical Property:

• Appearance/Colour: White crystal
• Vapor Pressure: 1.66E-12mmHg at 25°C
• Melting Point: 178-183℃
• Refractive Index: 1.588
• Boiling Point: 540.3 °C at 760 mmHg
• PKA: 12.05±0.20(Predicted)
• Flash Point: 280.6 °C
• PSA: 75.63000
• Density: 1.236 g/cm³
• LogP: 2.08250
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: DMSO (Slightly), Ethyl Acetate (Slightly, Heated), Methanol (Slightly)
• XLogP3: 2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 299.11575802
• Heavy Atom Count: 22
• Complexity: 373

Purity/Quality:

99% ^*data from raw suppliers

(2R,3S)-N-Benzoyl-3-phenylIsoserineMethylEster ^*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)NC(=O)C2=CC=CC=C2)O
• Uses: (2R,3S)-N-Benzoyl-3-phenyl Isoserine Methyl Ester is an intermediate in the preparation of potent anticancer drug Paclitaxel (P132500) used to study the location of the binding sites.

Technology Process of Methyl (2r,3s)-3-(benzoylamino)-2-hydroxy-3-phenylpropanoate

There total 199 articles about Methyl (2r,3s)-3-(benzoylamino)-2-hydroxy-3-phenylpropanoate 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: 92.0%

methyl (2R,3S)-2-acetoxy-3-phenyl-3-benzoylaminopropanoate (146848-86-4) → methyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate (32981-85-4)

Guidance literature:

With sodium methylate; In methanol; at 20 ℃; for 1h;

DOI:10.1021/ol035554w

Reference yield: 90.0%

(4S,5R)-2,4-diphenyl-2-oxazoline-5-carboxylic acid methyl ester (146848-91-1) → methyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate (32981-85-4)

Guidance literature:

With hydrogenchloride; In methanol; for 2h; Heating;

DOI:10.1016/S0957-4166(00)00418-3

Reference yield: 90.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + (2R,3S)-N-benzoyl-3-phenylisoserine (132201-33-3) → methyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate (32981-85-4)

Guidance literature:

In tetrahydrofuran; diethyl ether;

upstream raw materials:

methanol

sodium methylate

(+)-cis-1-benzoyl-3-acetoxy-4-phenylazetidin-2-one

taxol

Downstream raw materials:

Methyl (2S,4S,5R)-3-benzoyl-2-(p-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylate

Methyl (2R,4S,5R)-3-benzoyl-2-(p-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylate

N-benzoyl-(2R^*,3S^*)-3-phenylisoserine

(4S,5R)-3-Benzoyl-2,2-dimethyl-4-phenyl-1,3-oxazolidine-5-carboxylic acid

Refernces

• 1、 -. "Synthesis method of paclitaxel side chain and analogs thereof (by machine translation)". Paragraph 0053; 0079-0082. . Retrieved 2020/10/14.
• 2、 Weng, Shiue-Shien,Li, Hsin-Chun,Yang, Teng-Mao. "Chemoselective esterification of α-hydroxyacids catalyzed by salicylaldehyde through induced intramolecularity". . p. 1976 - 1986. Retrieved 2013/03/13.