(5R)-N-benzyl-N-(tert-butyloxycarbonyl)-5-diphenylphosphatoxy-6-methyl-6-nitroheptylamine

Base Information

• Chemical Name: (5R)-N-benzyl-N-(tert-butyloxycarbonyl)-5-diphenylphosphatoxy-6-methyl-6-nitroheptylamine
• CAS No.: 615268-21-8
• Molecular Formula: C₃₂H₄₁N₂O₈P
• Molecular Weight: 612.66
• Mol file: 615268-21-8.mol

Synonyms:(5R)-N-benzyl-N-(tert-butyloxycarbonyl)-5-diphenylphosphatoxy-6-methyl-6-nitroheptylamine

Chemical Property of (5R)-N-benzyl-N-(tert-butyloxycarbonyl)-5-diphenylphosphatoxy-6-methyl-6-nitroheptylamine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5R)-N-benzyl-N-(tert-butyloxycarbonyl)-5-diphenylphosphatoxy-6-methyl-6-nitroheptylamine

There total 4 articles about (5R)-N-benzyl-N-(tert-butyloxycarbonyl)-5-diphenylphosphatoxy-6-methyl-6-nitroheptylamine 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: 99.0%

chlorophosphoric acid diphenyl ester (2524-64-3) + (5R)-N-benzyl-N-(tert-butyloxycarbonyl)-5-hydroxy-6-methyl-6-nitroheptylamine (615268-19-4) → (5R)-N-benzyl-N-(tert-butyloxycarbonyl)-5-diphenylphosphatoxy-6-methyl-6-nitroheptylamine (615268-21-8)

Guidance literature:

With dmap; In dichloromethane; at 20 ℃;

DOI:10.1021/ol035564x

Reference yield:

benzyl-(5-oxo-pentyl)-carbamic acid tert-butyl acid (213772-26-0) → (5R)-N-benzyl-N-(tert-butyloxycarbonyl)-5-diphenylphosphatoxy-6-methyl-6-nitroheptylamine (615268-21-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 92 percent / potassium tert-butoxide / acetonitrile; 2-methyl-propan-2-ol

2: 93 percent / oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / 1.33 h / cooling

3: (S)-(-)-α,α-diphenyl-2-pyrrolidinemethanol; borane dimethyl sulfide complex / tetrahydrofuran / 0.83 h / Heating

4: DMAP / CH₂Cl₂ / 20 °C

With dmap; oxalyl dichloride; (S)-diphenylprolinol; dimethylsulfide borane complex; potassium tert-butylate; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; acetonitrile; tert-butyl alcohol; 1: Henry reaction / 2: Swern oxidation;

DOI:10.1016/j.tet.2006.03.063

Reference yield:

N-benzyl-N-(tert-butyloxycarbonyl)-5-hydroxy-6-methyl-6-nitroheptylamine (615268-16-1) → (5R)-N-benzyl-N-(tert-butyloxycarbonyl)-5-diphenylphosphatoxy-6-methyl-6-nitroheptylamine (615268-21-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 93 percent / oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / 1.33 h / cooling

2: (S)-(-)-α,α-diphenyl-2-pyrrolidinemethanol; borane dimethyl sulfide complex / tetrahydrofuran / 0.83 h / Heating

3: DMAP / CH₂Cl₂ / 20 °C

With dmap; oxalyl dichloride; (S)-diphenylprolinol; dimethylsulfide borane complex; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; 1: Swern oxidation;

DOI:10.1016/j.tet.2006.03.063

upstream raw materials:

chlorophosphoric acid diphenyl ester

(5R)-N-benzyl-N-(tert-butyloxycarbonyl)-5-hydroxy-6-methyl-6-nitroheptylamine

benzyl-(5-oxo-pentyl)-carbamic acid tert-butyl acid

N-benzyl-N-(tert-butyloxycarbonyl)-6-methyl-6-nitro-5-oxo-heptylamine

Downstream raw materials:

(5R)-N-benzyl-5-diphenylphosphatoxy-6-methyl-6-nitroheptylamine