N-[(2S,4S)-4-[2-(benzyloxycarbonyl)pyrrolidinyl]]-(1R)-[(tert-butyldiphenylsilyloxy)methyl]-2-aminoethylamine

Base Information

• Chemical Name: N-[(2S,4S)-4-[2-(benzyloxycarbonyl)pyrrolidinyl]]-(1R)-[(tert-butyldiphenylsilyloxy)methyl]-2-aminoethylamine
• CAS No.: 288582-55-8
• Molecular Formula: C₃₁H₄₁N₃O₃Si
• Molecular Weight: 531.77
• Mol file: 288582-55-8.mol

Synonyms:N-[(2S,4S)-4-[2-(benzyloxycarbonyl)pyrrolidinyl]]-(1R)-[(tert-butyldiphenylsilyloxy)methyl]-2-aminoethylamine

Chemical Property of N-[(2S,4S)-4-[2-(benzyloxycarbonyl)pyrrolidinyl]]-(1R)-[(tert-butyldiphenylsilyloxy)methyl]-2-aminoethylamine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-[(2S,4S)-4-[2-(benzyloxycarbonyl)pyrrolidinyl]]-(1R)-[(tert-butyldiphenylsilyloxy)methyl]-2-aminoethylamine

There total 3 articles about N-[(2S,4S)-4-[2-(benzyloxycarbonyl)pyrrolidinyl]]-(1R)-[(tert-butyldiphenylsilyloxy)methyl]-2-aminoethylamine 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%

N-[(2S,4S)-4-[2-(benzyloxycarbonyl)-1-(tert-butyloxycarbonyl)pyrrolidinyl]]-(1R)-[(tert-butyldiphenylsilyloxy)methyl]-2-(tert-butyloxycarbonyl)aminoethylamine (288582-54-7) → N-[(2S,4S)-4-[2-(benzyloxycarbonyl)pyrrolidinyl]]-(1R)-[(tert-butyldiphenylsilyloxy)methyl]-2-aminoethylamine (288582-55-8)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 0 - 20 ℃;

DOI:10.1021/jo000071g

Reference yield:

O-(tert-butyldiphenylsilyl)-(2R)-amino-3-(tert-butyloxycarbonyl)aminopropanol (288582-53-6) → N-[(2S,4S)-4-[2-(benzyloxycarbonyl)pyrrolidinyl]]-(1R)-[(tert-butyldiphenylsilyloxy)methyl]-2-aminoethylamine (288582-55-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: (CF₃SO₂)2O; diisopropylethylamine / CH₂Cl₂ / 1 h / -30 °C

1.2: 68 percent / diisopropylethylamine / CH₂Cl₂ / 72 h / 0 °C

2.1: 100 percent / CF₃COOH / CH₂Cl₂ / 0 - 20 °C

With trifluoromethylsulfonic anhydride; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In dichloromethane; 1.1: sulfonation / 1.2: Substitution / 2.1: carbamate cleavage;

DOI:10.1021/jo000071g

Reference yield:

O-(tert-butyldiphenylsilyl)-(2R)-triphenylmethylamino-3-(tert-butyloxycarbonyl)aminopropanol (288582-52-5) → N-[(2S,4S)-4-[2-(benzyloxycarbonyl)pyrrolidinyl]]-(1R)-[(tert-butyldiphenylsilyloxy)methyl]-2-aminoethylamine (288582-55-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 88 percent / BF₃*OEt₂; AcOH / CH₂Cl₂ / 2 h / 0 °C

2.1: (CF₃SO₂)2O; diisopropylethylamine / CH₂Cl₂ / 1 h / -30 °C

2.2: 68 percent / diisopropylethylamine / CH₂Cl₂ / 72 h / 0 °C

3.1: 100 percent / CF₃COOH / CH₂Cl₂ / 0 - 20 °C

With trifluoromethylsulfonic anhydride; boron trifluoride diethyl etherate; acetic acid; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In dichloromethane; 1.1: detritylation / 2.1: sulfonation / 2.2: Substitution / 3.1: carbamate cleavage;

DOI:10.1021/jo000071g

upstream raw materials:

N-[(2S,4S)-4-[2-(benzyloxycarbonyl)-1-(tert-butyloxycarbonyl)pyrrolidinyl]]-(1R)-[(tert-butyldiphenylsilyloxy)methyl]-2-(tert-butyloxycarbonyl)aminoethylamine

O-(tert-butyldiphenylsilyl)-(2R)-amino-3-(tert-butyloxycarbonyl)aminopropanol

O-(tert-butyldiphenylsilyl)-(2R)-triphenylmethylamino-3-(tert-butyloxycarbonyl)aminopropanol