(3R,4S)-3-[(Triethylsilyl)oxy]-4-phenyl-2-azetidinone

Base Information

• Chemical Name: (3R,4S)-3-[(Triethylsilyl)oxy]-4-phenyl-2-azetidinone
• CAS No.: 149140-54-5
• Molecular Formula: C15H23 N O2 Si
• Molecular Weight: 277.439
• DSSTox Substance ID: DTXSID50445487
• Nikkaji Number: J1.541.496K
• Wikidata: Q82263913
• Mol file: 149140-54-5.mol

Synonyms:149140-54-5;(3R,4S)-3-[(TRIETHYLSILYL)OXY]-4-PHENYL-2-AZETIDINONE;(3R-cis)-4-Phenyl-3-[(triethylsilyl)oxy]-2-azetidinone;(3R,4S)-4-phenyl-3-triethylsilyloxyazetidin-2-one;(3R,4S)-4-Phenyl-3-triethylsilyloxy-2-azetidinone;(3R,4S)-4-Phenyl-3-[(triethylsilyl)oxy]azetidin-2-one;Cis-4-phenyl-3-triethylsilanyloxy-2-zaetidin-2-one;SCHEMBL3088031;DTXSID50445487;FZWHCVWKYWKZHE-UONOGXRCSA-N;AKOS015966920;J-501272;(3R, 4S)-4-Phenyl-3-triethylsilyloxy-2-azetidinone;(3R,4S)-3-(Triethylsilyloxy)-4-phenylazetidine-2-one;661489-72-1

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

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 69-72°C
• Refractive Index: 1.516
• Boiling Point: 393.216°C at 760 mmHg
• PKA: 13.56±0.60(Predicted)
• Flash Point: 191.611°C
• PSA: 41.82000
• Density: 1.04g/cm³
• LogP: 3.52380
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 6
• Exact Mass: 277.149805511
• Heavy Atom Count: 19
• Complexity: 303

Purity/Quality:

99% ^*data from raw suppliers

(3R,4S)-3-[(Triethylsilyl)oxy]-4-phenyl-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(NC1=O)C2=CC=CC=C2
• Isomeric SMILES: CC[Si](CC)(CC)O[C@@H]1[C@@H](NC1=O)C2=CC=CC=C2
• Uses: (3R,4S)-3-[(Triethylsilyl)oxy]-4-phenyl-2-azetidinone (cas# 149140-54-5) is a compound useful in organic synthesis.

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

There total 12 articles about (3R,4S)-3-[(Triethylsilyl)oxy]-4-phenyl-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: 99.4%

triethylsilyl chloride (994-30-9) + (3R,4S)-3-hydroxy-4-phenylazetidin-2-one (132127-34-5) → (3R,4S)-3-triethylsilyloxy-4-phenylazetidin-2-one (149140-54-5)

Guidance literature:

With 1H-imidazole; In tetrahydrofuran; at 0 - 20 ℃; for 2.3h;

DOI:10.1002/jlcr.2580341010

Reference yield: 92.0%

C16H27NO3Si → (3R,4S)-3-triethylsilyloxy-4-phenylazetidin-2-one (149140-54-5)

Guidance literature:

With n-butyllithium; cytisine; In tetrahydrofuran; at 0 ℃; for 1h; Temperature; Solvent; Inert atmosphere; Cooling with ice;

Reference yield: 91.0%

methyl (2R,3S)-3-amino-3-phenyl-2-(triethylsilyloxy)propanoate (350583-44-7) → (3R,4S)-3-triethylsilyloxy-4-phenylazetidin-2-one (149140-54-5)

Guidance literature:

With lithium chloride; lithium hexamethyldisilazane; In tetrahydrofuran; at 0 ℃; for 4h; Temperature; Reagent/catalyst; Solvent; Inert atmosphere;

upstream raw materials:

triethylsilyl chloride

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

methyl (2R,3S)-3-amino-3-phenyl-2-(triethylsilyloxy)propanoate

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

Downstream raw materials:

(3R,4S)-1-neopentylcarbonyl-4-phenyl-3-triethylsilyloxyazetidin-2-one

(3R,4S)-1-(2-allylbenzoyl)-3-triethylsilyloxy-4-phenylazetidin-2-one

(3R,4S)-1-(2-allyloxybenzoyl)-3-triethylsilyloxy-4-phenylazetidin-2-one

(3R,4S)-1-(2-ethenylbenzoyl)-3-triethylsilyloxy-4-phenylazetidin-2-one

Refernces

• 1、 -. "A four-membered ring taxol alkane side chain compound preparation method". Page/Page column 4-8. . Retrieved 2017/11/16.
• 2、 Paterson, Ian,Naylor, Guy J.,Fujita, Takeshi,Guzman, Esther,Wright, Amy E.. "Total synthesis of a library of designed hybrids of the microtubule-stabilising anticancer agents taxol, discodermolide and dictyostatin". supporting information; experimental part. p. 261 - 263. Retrieved 2010/05/01.