(3R,4S)-3-Hydroxy-4-phenyl-2-azetidinone

Base Information

• Chemical Name: (3R,4S)-3-Hydroxy-4-phenyl-2-azetidinone
• CAS No.: 132127-34-5
• Molecular Formula: C9H9NO2
• Molecular Weight: 163.176
• Hs Code.: 2933790090
• European Community (EC) Number: 833-742-6
• DSSTox Substance ID: DTXSID50436855
• Nikkaji Number: J525.201F
• Wikidata: Q72480952
• Mol file: 132127-34-5.mol

Synonyms:132127-34-5;(3R,4S)-3-Hydroxy-4-phenyl-2-azetidinone;(3R,4S)-3-Hydroxy-4-phenylazetidin-2-one;(3R-cis)-3-Hydroxy-4-phenyl-2-azetidinone;133161-35-0;2-Azetidinone, 3-hydroxy-4-phenyl-, (3R,4S)-;SCHEMBL2112084;DTXSID50436855;FBZSDKXFQUKDLD-JGVFFNPUSA-N;AMY16033;MFCD07368374;AKOS006307811;AC-9031;DS-15677;3alpha-Hydroxy-4alpha-phenylazetidin-2-one;CS-0130887;H1656;2-Azetidinone,3-hydroxy-4-phenyl-, (3R,4S)-;J-501264

Chemical Property of (3R,4S)-3-Hydroxy-4-phenyl-2-azetidinone

Chemical Property:

• Appearance/Colour: White solid
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 187-188 °C
• Refractive Index: 1.612
• Boiling Point: 430.414 °C at 760 mmHg
• PKA: 11.86±0.40(Predicted)
• Flash Point: 214.107 °C
• PSA: 49.33000
• Density: 1.309 g/cm³
• LogP: 0.54720
• Storage Temp.: Refrigerator
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 163.063328530
• Heavy Atom Count: 12
• Complexity: 187

Purity/Quality:

99% ^*data from raw suppliers

(3R,4S)-3-Hydroxy-4-phenyl-2-azetidinone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C2C(C(=O)N2)O
• Isomeric SMILES: C1=CC=C(C=C1)[C@H]2[C@H](C(=O)N2)O
• Uses: Docetaxel or Paclitaxel intermediate Docetaxel or Paclitaxel intermediate.

Technology Process of (3R,4S)-3-Hydroxy-4-phenyl-2-azetidinone

There total 29 articles about (3R,4S)-3-Hydroxy-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: 100.0%

(3R,4S)-3-triisopropylsilyloxy-4-phenylazetidin-2-one (132127-31-2) → (3R,4S)-3-hydroxy-4-phenylazetidin-2-one (132127-34-5)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran;

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

Reference yield: 90.0%

(3R,4S)-3-<(tert-butyldimethylsilyl)oxy>-4-phenylazetidin-2-one (132127-30-1) → (3R,4S)-3-hydroxy-4-phenylazetidin-2-one (132127-34-5)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 0.25h;

DOI:10.1016/j.tet.2007.05.031

Reference yield: 82.0%

(3R-cis)-3-acetyloxy-4-phenyl-2-azetidinone (144790-01-2,133066-59-8) → (3R,4S)-3-hydroxy-4-phenylazetidin-2-one (132127-34-5)

Guidance literature:

With sodium hydrogencarbonate; sodium carbonate; Ambient temperature;

DOI:10.1016/S0957-4166(98)00049-4

upstream raw materials:

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

3-Triisopropylsilyloxy-4-phenylazetidin-2-one

(3R-cis)-3-acetyloxy-4-phenyl-2-azetidinone

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

Downstream raw materials:

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

(2R,3S)-3-phenylisoserine hydrochloride

(3R,4S)-4-cyclohexyl-3-hydroxy-2-azetidinone

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

Refernces

• 1、 Hata, Seiji,Tomioka, Kiyoshi. "Asymmetric synthesis of 3-amino-2-hydroxyalkanoates by Mannich reaction of menthyl acetate with imines and subsequent oxidation". . p. 8514 - 8520. Retrieved 2008/02/09.
• 2、 Martin-Zamora, Eloisa,Ferrete, Ana,Llera, Jose M.,Munoz, Jesus M.,Pappalardo, Rafael R.,Fernandez, Rosario,Lassaletta, Jose M.. "Studies on stereoselective [2+2] cycloadditions between N,N-dialkylhydrazones and ketenes". . p. 6111 - 6129. Retrieved 2007/10/03.