3-Phenyl-2-(phenylsulfonyl)-1,2-oxaziridine

Base Information

• Chemical Name: 3-Phenyl-2-(phenylsulfonyl)-1,2-oxaziridine
• CAS No.: 63160-13-4
• Molecular Formula: C13H11NO3S
• Molecular Weight: 622.739
• Hs Code.: 2934999090
• European Community (EC) Number: 862-503-9
• NSC Number: 377129,268112
• DSSTox Substance ID: DTXSID10313234
• Nikkaji Number: J274.580A
• Wikipedia: Davis_reagent
• Wikidata: Q72498172
• Mol file: 63160-13-4.mol

Synonyms:3-Phenyl-2-(phenylsulfonyl)-1,2-oxaziridine;63160-13-4;2-(benzenesulfonyl)-3-phenyloxaziridine;3-Phenyl-2-(phenylsulfonyl)-oxaziridine;Davis oxaziridine;3-phenyl-2-(phenylsulfonyl)Oxaziridine;2-(benzenesulfonyl)-3-phenyl-oxaziridine;80997-75-7;MFCD03931864;Oxaziridine, 3-phenyl-2-(phenylsulfonyl)-;NSC 268112;2-(Phenylsulfonyl)-3-phenyloxaziridine;NSC377129;SCHEMBL113055;SCHEMBL2338341;SCHEMBL13663248;DTXSID10313234;AMY19075;BCP25532;N-(benzenesulfonyl)phenyloxaziridine;2-phenylsulfonyl-3-phenyloxaziridine;3-phenyl-2-phenylsulfonyloxaziridine;phenyl-2-(phenylsulfonyl)oxaziridine;2-benzenesulfonyl-3-phenyloxaziridine;3-phenyl-2-phenylsulphonyloxaziridine;NSC268112;2-(Phenysulfonyl)-3-phenyloxaziridine;2-benzenesulfonyl-3-phenyl-oxaziridine;AKOS015855754;GS-3937;NSC-268112;NSC-377129;SB13078;2-Benzenesulphonyl-3-phenyl-oxaziridine;2-(phenylsulfonyl)-3-phenyl-oxaziridine;3-phenyl-2-(phenyl-sulfonyl)oxaziridine;AC-25497;SY026452;3-phenyl-2-(phenylsulfonyl)-1,2oxaziridine;3-phenyl-2-(phenysulfonyl)-1,2-oxaziridine;CS-0019264;FT-0652968;racemic 2-benzenesulfonyl-3-phenyloxaziridine;A19001;EN300-175119;J-513037

Chemical Property of 3-Phenyl-2-(phenylsulfonyl)-1,2-oxaziridine

Chemical Property:

• Vapor Pressure: 1.99E-06mmHg at 25°C
• Melting Point: 96-97 °C
• Refractive Index: 1.654
• Boiling Point: 394.4 °C at 760 mmHg
• PKA: -13.47±0.40(Predicted)
• Flash Point: 192.3 °C
• PSA: 58.06000
• Density: 1.398 g/cm³
• LogP: 3.34000
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly, Sonicated)
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 261.04596439
• Heavy Atom Count: 18
• Complexity: 378

Purity/Quality:

97% ^*data from raw suppliers

DavisOxaziridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C2N(O2)S(=O)(=O)C3=CC=CC=C3
• Uses: 3-Phenyl-2-(phenylsulfonyl)-1,2-oxaziridine, is an oxidizing agent used in the preparation of wide variety of pharmaceutical compounds. Davis Oxaziridine is an oxidizing agent used in the preparation of wide variety of pharmaceutical compounds.

Technology Process of 3-Phenyl-2-(phenylsulfonyl)-1,2-oxaziridine

There total 5 articles about 3-Phenyl-2-(phenylsulfonyl)-1,2-oxaziridine 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:

(S)-4-benzyl-3-{3-[(2S,5R)-5-(4-methoxybenzyloxy)-1-(toluene-4-sulphonyl)piperidin-2-yl]propionyl}oxazolidin-2-one (959937-89-4) → (S)-4-benzyl-3-{(S)-2-hydroxy-3-[(2S,5R)-5-(4-methoxy-benzyloxy)-1-(toluene-4-sulfonyl)-piperidin-2-yl]-propionyl}-oxazolidin-2-one (63160-13-4)

Guidance literature:

(S)-4-benzyl-3-{3-[(2S,5R)-5-(4-methoxybenzyloxy)-1-(toluene-4-sulphonyl)piperidin-2-yl]propionyl}oxazolidin-2-one; With sodium hexamethyldisilazane; In tetrahydrofuran; at -78 - -40 ℃; for 0.75h;

With N-(benzenesulfonyl)-3-phenyloxaziridine; In tetrahydrofuran; at -78 ℃; for 2h;

Reference yield:

3-[(2S,5R)-5-(4-methoxybenzyloxy)-1-(toluene-4-sulphonyl)piperidin-2-yl]propionic acid (959937-90-7) → (S)-4-benzyl-3-{(S)-2-hydroxy-3-[(2S,5R)-5-(4-methoxy-benzyloxy)-1-(toluene-4-sulfonyl)-piperidin-2-yl]-propionyl}-oxazolidin-2-one (63160-13-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: triethylamine / diethyl ether; dichloromethane / 1.08 h / -78 - 0 °C

2.1: n-butyllithium / tetrahydrofuran; hexane / 0.75 h / -78 °C

2.2: 3 h / -78 - 20 °C

3.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.75 h / -78 - -40 °C

3.2: 2 h / -78 °C

With n-butyllithium; sodium hexamethyldisilazane; triethylamine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane;

Reference yield:

C28H37NO7S → (S)-4-benzyl-3-{(S)-2-hydroxy-3-[(2S,5R)-5-(4-methoxy-benzyloxy)-1-(toluene-4-sulfonyl)-piperidin-2-yl]-propionyl}-oxazolidin-2-one (63160-13-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 0.75 h / -78 °C

1.2: 3 h / -78 - 20 °C

2.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.75 h / -78 - -40 °C

2.2: 2 h / -78 °C

With n-butyllithium; sodium hexamethyldisilazane; In tetrahydrofuran; hexane;

upstream raw materials:

N-benzylidenephenylsulfonamide

(S)-4-benzyl-3-{3-[(2S,5R)-5-(4-methoxybenzyloxy)-1-(toluene-4-sulphonyl)piperidin-2-yl]propionyl}oxazolidin-2-one

3-[(2S,5R)-5-(4-methoxybenzyloxy)-1-(toluene-4-sulphonyl)piperidin-2-yl]propionic acid

Downstream raw materials:

(S)-4-benzyl-3-{(S)-2-methoxy-3-[(2S,5R)-5-(4-methoxy-benzyloxy)-1-(toluene-4-sulfonyl)-piperidin-2-yl]-propionyl}-oxazolidin-2-one

Refernces

Stereoselective synthesis of amphiasterin B4: Assignment of absolute configuration

10.1016/j.tetlet.2010.10.098

The research focuses on the first asymmetric synthesis of (+)-amphiasterin B4, a cytotoxic metabolite isolated from a marine sponge, using a chiral pool strategy to prepare the enantiomerically pure form of this compound. The purpose of this study was to synthesize amphiasterin B4 and determine its absolute stereochemistry, which was previously unspecified. The researchers successfully synthesized (+)-amphiasterin B4, starting from a known (S)-b-benzyloxy-γ-lactone, and confirmed the identity and stereochemistry of the synthesized product by comparing it with the properties of the authentic material. The conclusion was that the absolute configurations of the naturally occurring amphiasterin B4 should be assigned as 3R, 4R, and 5S. Key chemicals used in the synthesis process included dihydroxyacetone dimer, (S)-(-)-α-methylbenzylamine, 2-phenylsulfonyl-3-phenyloxaziridine, methylmagnesium bromide, sodium borohydride, and various protecting groups such as THP, TBDPS, TBS, and catalytic reagents like PDC and PTSA.

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