(3R,4S)-1-Benzoyl-4-phenyl-3-[(triethylsilyl)oxy]-2-azetidinone

Base Information

• Chemical Name: (3R,4S)-1-Benzoyl-4-phenyl-3-[(triethylsilyl)oxy]-2-azetidinone
• CAS No.: 149249-91-2
• Molecular Formula: C22H27NO3Si
• Molecular Weight: 381.547
• DSSTox Substance ID: DTXSID30440915
• Nikkaji Number: J736.888G
• Wikidata: Q72440460
• Mol file: 149249-91-2.mol

Synonyms:149249-91-2;(3R,4S)-1-BENZOYL-4-PHENYL-3-[(TRIETHYLSILYL)OXY]-2-AZETIDINONE;(3R,4S)-1-benzoyl-4-phenyl-3-triethylsilyloxyazetidin-2-one;2-Azetidinone, 1-benzoyl-4-phenyl-3-[(triethylsilyl)oxy]-, (3R,4S)-;(3R,4S)-1-Benzoyl-4-phenyl-3-[(triethylsilyl)-oxy]-2-azetidinone;SCHEMBL4366611;DTXSID30440915;AMY16037;MFCD08273950;(3R,4S)-1-BENZOYL-4-PHENYL-3-(TRIETHYLSILYLOXY)AZETIDIN-2-ONE;AKOS016843304;AC-23878;AS-15777;CS-0130890;F13009;A808868;J-501260;(3R, 4S)-1-Benzoyl-4-phenyl-3-triethylsilyloxy-2-azetidinone;1-Benzoyl-3alpha-(triethylsiloxy)-4alpha-phenylazetidin-2-one;(3R,4S)-1-Benzoyl-4-phenyl-3-((triethylsilyl)oxy)azetidin-2-one

Chemical Property of (3R,4S)-1-Benzoyl-4-phenyl-3-[(triethylsilyl)oxy]-2-azetidinone

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.567
• Boiling Point: 467.227 °C at 760 mmHg
• PKA: -4.66±0.60(Predicted)
• Flash Point: 236.371 °C
• PSA: 46.61000
• Density: 1.13 g/cm³
• LogP: 4.73860
• Storage Temp.: 2-8°C
• Solubility.: Dichloromethane, Ether, Ethyl Acetate, Methanol
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 7
• Exact Mass: 381.17602026
• Heavy Atom Count: 27
• Complexity: 513

Purity/Quality:

99% ^*data from raw suppliers

(3R,4S)-1-Benzoyl-4-phenyl-3-[(triethylsilyl)oxy]-2-azetidinone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC[Si](CC)(CC)OC1C(N(C1=O)C(=O)C2=CC=CC=C2)C3=CC=CC=C3
• Isomeric SMILES: CC[Si](CC)(CC)O[C@@H]1[C@@H](N(C1=O)C(=O)C2=CC=CC=C2)C3=CC=CC=C3
• Uses: (3R,4S)-1-Benzoyl-4-phenyl-3-[(triethylsilyl)oxy]-2-azetidinone is an intermedaite of 10-O-[(2R,3S)-3-(Benzoylamino)-2-hydroxy-3-phenylpropanoyl]-10-O-deacetylpaclitaxel (B207800), which is an impurity in the synthesis of Paclitaxel (P132500), an antineoplastic. Used in the study of structure and function of microtubles into tubulin. Paclitaxel is now used to treat patients with lung, ovarian, breast cancer, head and neck cancer, and advanced forms of Kaposi''s sarcoma.

Technology Process of (3R,4S)-1-Benzoyl-4-phenyl-3-[(triethylsilyl)oxy]-2-azetidinone

There total 12 articles about (3R,4S)-1-Benzoyl-4-phenyl-3-[(triethylsilyl)oxy]-2-azetidinone 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: 98.0%

benzoyl chloride (98-88-4) + (3R,4S)-3-triethylsilyloxy-4-phenylazetidin-2-one (149140-54-5) → (3R,4S)-1-benzoyl-4-phenyl-3-(triethylsilyl)oxy-2-azetidinone (149249-91-2)

Guidance literature:

With triethylamine;

DOI:10.1016/S0040-4039(98)00548-6

Reference yield:

(3R,4S)-4-phenyl-3-triethylsilyoxy-2-azetidinone + benzoyl chloride (98-88-4) + (3R,4S)-3-triethylsilyloxy-4-phenylazetidin-2-one (149140-54-5) → (3R,4S)-1-benzoyl-4-phenyl-3-(triethylsilyl)oxy-2-azetidinone (149249-91-2)

Guidance literature:

With dmap; N-ethyl-N,N-diisopropylamine; In dichloromethane;

Reference yield:

triethylsilyl chloride (994-30-9) → (3R,4S)-1-benzoyl-4-phenyl-3-(triethylsilyl)oxy-2-azetidinone (149249-91-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 96 percent / triethylamine / tetrahydrofuran

2.1: 2.58 g / H₂ / Pd/C / ethyl acetate / 20 h

3.1: trimethylsilyl chloride / diethyl ether / 1 h / 20 °C

3.2: 62 percent / tert-butylmagnesium chloride / diethyl ether / 3 h / 20 °C

4.1: 87 percent / triethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 20 h / 20 °C

With dmap; chloro-trimethyl-silane; hydrogen; triethylamine; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; dichloromethane; ethyl acetate;

DOI:10.1002/1099-0690(200105)2001:9<1761::AID-EJOC1761>3.0.CO;2-O

upstream raw materials:

benzoyl chloride

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

triethylsilyl chloride

Methyl (2R,3S)-(+)-2-hydroxy-3-azido-3-phenyl-propionate

Downstream raw materials:

C₅₆H₇₃NO₁₄Si

C₅₄H₇₇NO₁₄Si₂

7,9-diacetyl-9(R)-dihydro-2'-triethylsilyl-1-deoxypaclitaxel

2’-TES-7-TROC-taxol