(2R,4S,5R)-4-methyl-3-(4-methylphenyl)sulfonyl-5-phenyloxathiazolidine 2-oxide

Base Information

• Chemical Name: (2R,4S,5R)-4-methyl-3-(4-methylphenyl)sulfonyl-5-phenyloxathiazolidine 2-oxide
• CAS No.: 473554-15-3
• Molecular Formula: C₁₆H₁₇NO₄S₂
• Molecular Weight: 351.447
• DSSTox Substance ID: DTXSID50461440
• Wikidata: Q82285785
• Mol file: 473554-15-3.mol

Synonyms:CTK4I9882;473554-15-3;DTXSID50461440

Chemical Property of (2R,4S,5R)-4-methyl-3-(4-methylphenyl)sulfonyl-5-phenyloxathiazolidine 2-oxide

Chemical Property:

• XLogP3: 3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 351.05990037
• Heavy Atom Count: 23
• Complexity: 531

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1C(OS(=O)N1S(=O)(=O)C2=CC=C(C=C2)C)C3=CC=CC=C3
• Isomeric SMILES: C[C@H]1[C@H](O[S@@](=O)N1S(=O)(=O)C2=CC=C(C=C2)C)C3=CC=CC=C3

Technology Process of (2R,4S,5R)-4-methyl-3-(4-methylphenyl)sulfonyl-5-phenyloxathiazolidine 2-oxide

There total 2 articles about (2R,4S,5R)-4-methyl-3-(4-methylphenyl)sulfonyl-5-phenyloxathiazolidine 2-oxide 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:

N-((1R,2S)-1-hydroxy-1-phenylpropan-2-yl)-4-methylbenzene sulfonamide (108591-33-9) → (2R,4S,5R)-4-methyl-5-phenyl-3-(toluene-4-sulfonyl)oxathiazolidine-2-oxide (473554-15-3)

Guidance literature:

With pyridine; thionyl chloride; In tetrahydrofuran; at -78 ℃;

DOI:10.1002/anie.200250644

Reference yield:

N-((1R,2S)-1-hydroxy-1-phenylpropan-2-yl)-4-methylbenzene sulfonamide (108591-33-9) → (2R,4S,5R)-4-methyl-5-phenyl-3-(toluene-4-sulfonyl)oxathiazolidine-2-oxide (473554-15-3) + (2R,4S,5R)-4-Methyl-5-phenyl-3-(toluene-4-sulfonyl)-[1,2,3]oxathiazolidine 2-oxide

Guidance literature:

With thionyl chloride; 2,6-di-tert-butyl-pyridine; In tetrahydrofuran; at -45 ℃;

DOI:10.1002/anie.200250644

Reference yield: 99.0%

N,N-dimethyl-o-iodoaniline (698-02-2) + (2R,4S,5R)-4-methyl-5-phenyl-3-(toluene-4-sulfonyl)oxathiazolidine-2-oxide (473554-15-3) → (1R,2S)-2-(p-tolylsulfonylamino)-1-phenylpropyl (S)-2-(N,N-dimethylamino)phenyl sulfinate (642473-02-7)

Guidance literature:

N,N-dimethyl-o-iodoaniline; With iodine; magnesium; In diethyl ether; Heating;

(2R,4S,5R)-4-methyl-5-phenyl-3-(toluene-4-sulfonyl)oxathiazolidine-2-oxide; In tetrahydrofuran; diethyl ether; at -78 ℃; for 1h;

DOI:10.1021/ja038491l

upstream raw materials:

N-((1R,2S)-1-hydroxy-1-phenylpropan-2-yl)-4-methylbenzene sulfonamide

Downstream raw materials:

2-Methyl-propane-2-sulfinic acid (1R,2S)-1-phenyl-2-(toluene-4-sulfonylamino)-propyl ester

(1R,2S)-2-(p-tolylsulfonylamino)-1-phenylpropyl (S)-2-(N,N-dimethylamino)phenyl sulfinate

N-((1R,2S)-1-hydroxy-1-phenylpropan-2-yl)-4-methylbenzene sulfonamide

Adamantane-1-sulfinic acid (1R,2S)-1-phenyl-2-(toluene-4-sulfonylamino)-propyl ester