(4S,5R)-3-(tert-Butoxycarbonyl)-2-(4-methoxyphenyl)-4-phenyloxazolidine-5-carboxylic acid

Base Information

• Chemical Name: (4S,5R)-3-(tert-Butoxycarbonyl)-2-(4-methoxyphenyl)-4-phenyloxazolidine-5-carboxylic acid
• CAS No.: 196404-55-4
• Molecular Formula: C22H25NO6
• Molecular Weight: 399.444
• Hs Code.: 29349990
• European Community (EC) Number: 844-471-8
• DSSTox Substance ID: DTXSID10457445
• Nikkaji Number: J1.931.502I
• Mol file: 196404-55-4.mol

Synonyms:196404-55-4;(4S,5R)-3-(tert-Butoxycarbonyl)-2-(4-methoxyphenyl)-4-phenyloxazolidine-5-carboxylic acid;(4S,5R)-2-(4-methoxyphenyl)-3-[(2-methylpropan-2-yl)oxycarbonyl]-4-phenyl-1,3-oxazolidine-5-carboxylic acid;(4S,5R)-3-tert-Butoxycarbony-2-(4-anisyl)-4- phenyl-5-oxazolidine carboxylic acid;(4S,5R)-3-(tert-Butoxycarbonyl)-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylic acid;(4S,5R)-3-tert-Butoxycarbony-2-(4-anisyl)-4-phenyl-5-oxazolidinecarboxylic acid;SCHEMBL7134268;AMY9146;DTXSID10457445;MSVWUXLRSKRKFZ-PAMZHZACSA-N;MFCD09837613;AKOS015902337;AC-23877;AS-11439;CS-0022809;F13036;A880096;(4S,5R)-3-(tert-Butoxycarbonyl)-2-(4-methoxyphenyl)-4-phenyloxazolidine-5-carboxylicacid;(4S,5R)-3-tert-Butoxycarbonyl-2-(4-anisyl)-4-phenyl-5-oxazolidinecarboxylic acid;(4S,5R)-2-(4-Methoxyphenyl)-3-(tert-butyloxycarbonyl)-4-phenyloxazolidine-5-carboxylic acid

Chemical Property of (4S,5R)-3-(tert-Butoxycarbonyl)-2-(4-methoxyphenyl)-4-phenyloxazolidine-5-carboxylic acid

Chemical Property:

• Vapor Pressure: 5.25E-14mmHg at 25°C
• Melting Point: 134-138 °C
• Refractive Index: 1.567
• Boiling Point: 573.8 °C at 760 mmHg
• PKA: 2.99±0.60(Predicted)
• Flash Point: 300.8 °C
• PSA: 85.30000
• Density: 1.238 g/cm³
• LogP: 4.09350
• Storage Temp.: 2-8°C
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 6
• Exact Mass: 399.16818752
• Heavy Atom Count: 29
• Complexity: 574

Purity/Quality:

99% ^*data from raw suppliers

(4S,5R)-3-tert-Butoxycarbony-2-(4-anisyl)-4-phenyl-5-oxazolidineCarboxylicAcid ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1C(C(OC1C2=CC=C(C=C2)OC)C(=O)O)C3=CC=CC=C3
• Isomeric SMILES: CC(C)(C)OC(=O)N1[C@H]([C@@H](OC1C2=CC=C(C=C2)OC)C(=O)O)C3=CC=CC=C3
• Uses: (4S,5R)-3-tert-Butoxycarbony-2-(4-anisyl)-4-phenyl-5-oxazolidine carboxylic acid is an intermediate/impurity for docetaxel hydrate (D494420). It can also be used to synthesize quinoline-docetaxel analogues which exhibit anticancer activity.

Technology Process of (4S,5R)-3-(tert-Butoxycarbonyl)-2-(4-methoxyphenyl)-4-phenyloxazolidine-5-carboxylic acid

There total 17 articles about (4S,5R)-3-(tert-Butoxycarbonyl)-2-(4-methoxyphenyl)-4-phenyloxazolidine-5-carboxylic acid 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%

(2*,4S,5R)-methyl N-tert-butoxycarbonyl-2-(4'-methoxy)phenyl-4-phenyl-1,3-oxazolidine-5-methionate (670254-71-4,153652-75-6) → acide (4S,5R)-N-(tert-butoxycarbonyl)-2-(4-O-methoxyphenyl)-4-phenyl-5-oxazolidine carboxylique (196404-55-4)

Guidance literature:

With methanol; sodium hydroxide; at 20 ℃;

Reference yield: 67.9%

benzyl (4S,5R)-3-t-butoxycarbonyl-2-(4-methoxyphenyl)-4-phenyl-5-oxazolidine carboxylate (1531632-32-2) → acide (4S,5R)-N-(tert-butoxycarbonyl)-2-(4-O-methoxyphenyl)-4-phenyl-5-oxazolidine carboxylique (196404-55-4)

Guidance literature:

With hydrogen; palladium(II) hydroxide; In methanol; at 20 ℃; for 1h; under 103.432 Torr;

Reference yield:

benzyl 2R-hydroxy-3S-aminophenyl propionate → acide (4S,5R)-N-(tert-butoxycarbonyl)-2-(4-O-methoxyphenyl)-4-phenyl-5-oxazolidine carboxylique (196404-55-4)

Guidance literature:

Multi-step reaction with 3 steps

1: triethylamine / dichloromethane / 20 °C / Inert atmosphere

2: pyridinium p-toluenesulfonate / toluene / 4.33 h / 90 - 100 °C / Inert atmosphere

3: hydrogen; palladium(II) hydroxide / methanol / 1 h / 20 °C / 1034.32 Torr / Inert atmosphere

With hydrogen; palladium(II) hydroxide; pyridinium p-toluenesulfonate; triethylamine; In methanol; dichloromethane; toluene;

DOI:10.1016/j.bmc.2013.11.037

upstream raw materials:

(2*,4S,5R)-methyl N-tert-butoxycarbonyl-2-(4'-methoxy)phenyl-4-phenyl-1,3-oxazolidine-5-methionate

di-tert-butyl dicarbonate

methyl (2R,3S)-3-(tert-butoxycarbonylamino)-2-hydroxy-3-phenylpropionate

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

Downstream raw materials:

carbazitaxel

7,10-bis-O-(2,2,2-trichloroethoxycarbonyl)docetaxel

Docetaxel

7,10-di-O-(2-chlroacetyl)docetaxel

Refernces

• 1、 -. "TAXANE COMPOUND, AND PREPARATION METHOD AND USE THEREOF". Paragraph 0140; 0141. . Retrieved 2016/12/16.
• 2、 Jing, Yun-Rong,Zhou, Wei,Li, Wan-Liang,Zhao, Lin-Xiang,Wang, Yong-Feng. "The synthesis of novel taxoids for oral administration". . p. 194 - 203. Retrieved 2014/01/17.