(3R,4S)-Tert-butyl 3-(1-ethoxyethoxy)-2-oxo-4-phenylazetidine-1-carboxylate

Base Information

• Chemical Name: (3R,4S)-Tert-butyl 3-(1-ethoxyethoxy)-2-oxo-4-phenylazetidine-1-carboxylate
• CAS No.: 201856-57-7
• Molecular Formula: C18H25NO5
• Molecular Weight: 335.4
• DSSTox Substance ID: DTXSID10432979
• Mol file: 201856-57-7.mol

Synonyms:201856-57-7;(3R,4S)-TERT-BUTYL 3-(1-ETHOXYETHOXY)-2-OXO-4-PHENYLAZETIDINE-1-CARBOXYLATE;tert-Butyl (3R,4S)-3-(1-ethoxyethoxy)-2-oxo-4-phenylazetidine-1-carboxylate;(3R,4S)-3-(1-Ethoxyethoxy)-2-oxo-4-phenyl-1-azetidinecarboxylic Acid 1,1-DiMethylethyl Ester;(3R,4S)-1-Tert-Butoxycarbonyl-3-(1-Ethoxyethoxy)-4-Phenyl-2-Azetidinone;SCHEMBL3784269;AMY4255;DTXSID10432979;CZTZICYNMYGUNU-JQXSQYPDSA-N;AKOS016003591;AC-9030;CS-0449643;S10599;Q-200017;(3r,4s)-3-(1-ethoxyethoxy)-2-oxo-4-phenyl-1-azetidinecarboxylic acid tert-butyl ester;(3R,4S)-tert-butyl-3-(1-ethoxyethoxy)-2-oxo-4-phenylazetidine-1-carboxylate

Chemical Property of (3R,4S)-Tert-butyl 3-(1-ethoxyethoxy)-2-oxo-4-phenylazetidine-1-carboxylate

Chemical Property:

• Vapor Pressure: 1.25E-08mmHg at 25°C
• Refractive Index: 1.532
• Boiling Point: 459.592 °C at 760 mmHg
• PKA: -4.97±0.60(Predicted)
• Flash Point: 231.753 °C
• PSA: 65.07000
• Density: 1.161 g/cm³
• LogP: 3.21060
• Storage Temp.: 2-8°C
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 335.17327290
• Heavy Atom Count: 24
• Complexity: 453

Purity/Quality:

99% ^*data from raw suppliers

(3R,4S)-3-(1-Ethoxyethoxy)-2-oxo-4-phenyl-1-azetidinecarboxylicAcid1,1-DimethylethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(C)OC1C(N(C1=O)C(=O)OC(C)(C)C)C2=CC=CC=C2
• Isomeric SMILES: CCOC(C)O[C@@H]1[C@@H](N(C1=O)C(=O)OC(C)(C)C)C2=CC=CC=C2
• Uses: (3R,4S)-3-(1-Ethoxyethoxy)-2-oxo-4-phenyl-1-azetidinecarboxylic acid 1,1-Dimethylethyl ester is used as a reagent in the synthesis of abeo-taxane derivatives that possess broad inhibitory effects against proliferation of colon cancer, melanoma, and renal cancer cell lines. (3R,4S)-3-(1-Ethoxyethoxy)-2-oxo-4-phenyl-1-azetidinecarboxylic acid 1,1-Dimethylethyl ester is also used as a reagent in the synthesis of a novel D-ring modified Docetaxel (D494420) analogue which has proven to have equipotent cytotoxicity in relation to Paclitaxel (P132500) towards cancer cell lines.

Technology Process of (3R,4S)-Tert-butyl 3-(1-ethoxyethoxy)-2-oxo-4-phenylazetidine-1-carboxylate

There total 4 articles about (3R,4S)-Tert-butyl 3-(1-ethoxyethoxy)-2-oxo-4-phenylazetidine-1-carboxylate 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: 93.0%

di-tert-butyl dicarbonate (24424-99-5) + (3R,4S)-3-<((R*)-1'-ethoxyethyl)oxy>-4-phenyl-2-azetidinone (201856-48-6) → 1-tert-butoxycarbonyl-(3R,4S)-3-EEO-4-phenylazetidin-2-one (201856-57-7,152089-12-8)

Guidance literature:

With dmap; triethylamine; In dichloromethane;

DOI:10.1016/S0040-4039(00)60514-2

Reference yield:

(3R,4S)-3-hydroxy-4-phenylazetidin-2-one (132127-34-5) → 1-tert-butoxycarbonyl-(3R,4S)-3-EEO-4-phenylazetidin-2-one (201856-57-7,152089-12-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / H⁽¹⁺⁾

2: 93 percent / Et₃N, DMAP / CH₂Cl₂

With dmap; hydrogen cation; triethylamine; In dichloromethane;

DOI:10.1016/S0040-4039(00)60514-2

Reference yield:

(3R,4S)-3-triisopropylsilyloxy-4-phenylazetidin-2-one (132127-31-2) → 1-tert-butoxycarbonyl-(3R,4S)-3-EEO-4-phenylazetidin-2-one (201856-57-7,152089-12-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 100 percent / NBu₄F / tetrahydrofuran

2: 100 percent / H⁽¹⁺⁾

3: 93 percent / Et₃N, DMAP / CH₂Cl₂

With dmap; tetrabutyl ammonium fluoride; hydrogen cation; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1016/S0040-4039(00)60514-2

upstream raw materials:

di-tert-butyl dicarbonate

(3R,4S)-3-<((R^*)-1'-ethoxyethyl)oxy>-4-phenyl-2-azetidinone

(3R,4S)-3-hydroxy-4-phenylazetidin-2-one

(3R,4S)-3-triisopropylsilyloxy-4-phenylazetidin-2-one

Downstream raw materials:

2’-(1-ethoxyethyl)-7,10-(trichloroethoxycarbonyl)docetaxel

2'-EE-7,10-di-Boc-docetaxel

2'-EE-10-acetyl-7-Boc-docetaxel

C₄₇H₄₉NO₁₂

Refernces

• 1、 -. "Anti-tumor compounds, pharmaceutical compositions, methods for preparation thereof and for treatment". . . Retrieved 2008/06/13.
• 2、 Ojima, Iwao,Sun, Chung Ming,Zucco, Martine,Park, Young Boon,Duclos, Olivier,Kuduk, Scott. "A highly efficient route to taxotere by the β-lactam synthon method". . p. 4149 - 4152. Retrieved 2007/10/02.