Benzenesulfonamide, N-[(1R,2R)-1-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-2-hydroxy-2-( 4-nitrophenyl)ethyl]-4-methyl-

Base Information

• Chemical Name: Benzenesulfonamide, N-[(1R,2R)-1-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-2-hydroxy-2-( 4-nitrophenyl)ethyl]-4-methyl-
• CAS No.: 405176-15-0
• Molecular Formula: C22H32N2O6SSi
• Molecular Weight: 480.657
• Mol file: 405176-15-0.mol

Synonyms:

Chemical Property of Benzenesulfonamide, N-[(1R,2R)-1-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-2-hydroxy-2-( 4-nitrophenyl)ethyl]-4-methyl-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzenesulfonamide, N-[(1R,2R)-1-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-2-hydroxy-2-( 4-nitrophenyl)ethyl]-4-methyl-

There total 1 articles about Benzenesulfonamide, N-[(1R,2R)-1-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-2-hydroxy-2-( 4-nitrophenyl)ethyl]-4-methyl- 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: 77.0%

(1R,2R)-2-Amino-1-(4-nitrophenyl)-1,3-propanediol (119-62-0,716-61-0,2792-51-0,2792-52-1,2964-48-9,3689-55-2,63526-31-8,71115-69-0,140694-64-0) + tert-butyldimethylsilyl chloride (18162-48-6) + p-toluenesulfonyl chloride (98-59-9) → (1R,2R)-3-tert-butyldimethylsilyloxy-2-(4-methylphenyl)sulfamido-1-(4-nitrophenyl)-1-propanol (405176-15-0)

Guidance literature:

(1R,2R)-2-Amino-1-(4-nitrophenyl)-1,3-propanediol; p-toluenesulfonyl chloride; With triethylamine; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 21h;

tert-butyldimethylsilyl chloride; With 1H-imidazole; In N,N-dimethyl-formamide; at -5 - 50 ℃; for 24h; Further stages.;

DOI:10.1021/ol0170152

Reference yield: 83.0%

(1R,2R)-3-tert-butyldimethylsilyloxy-2-(4-methylphenyl)sulfamido-1-(4-nitrophenyl)-1-propanol (405176-15-0) → (2S,3S)-2-(tert-butyldimethylsilyloxy)methyl-1-(4-methylphenylsulfonyl)-3-(4-nitrophenyl)-aziridine

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 20 ℃; for 11h;

DOI:10.1021/ol0170152

Reference yield:

(1R,2R)-3-tert-butyldimethylsilyloxy-2-(4-methylphenyl)sulfamido-1-(4-nitrophenyl)-1-propanol (405176-15-0) → (2S,3S)-2-hydroxymethyl-1-(4-methylphenylsulfonyl)-3-(4-nitrophenyl)aziridine (405176-17-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 83 percent / PPh₃; diethylazodicarboxylate / tetrahydrofuran / 11 h / 20 °C

2: 94 percent / Bu₄N*HF / tetrahydrofuran / 0.5 h / 0 °C

With Bu₄N*HF; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran;

DOI:10.1021/ol0170152

upstream raw materials:

(1R,2R)-2-Amino-1-(4-nitrophenyl)-1,3-propanediol

tert-butyldimethylsilyl chloride

p-toluenesulfonyl chloride

Downstream raw materials:

(2S,3S)-2-hydroxymethyl-1-(4-methylphenylsulfonyl)-3-(4-nitrophenyl)aziridine