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

Base Information

Chemical Name:N-[(2S,4S)-4-[2-(benzyloxycarbonyl)-1-(tert-butyloxycarbonyl)pyrrolidinyl]]-(1R)-[(tert-butyldiphenylsilyloxy)methyl]-2-(tert-butyloxycarbonyl)aminoethylamine
CAS No.:288582-54-7
Molecular Formula:C₄₁H₅₇N₃O₇Si
Molecular Weight:732.005
Hs Code.:

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

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

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

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

There total 4 articles about N-[(2S,4S)-4-[2-(benzyloxycarbonyl)-1-(tert-butyloxycarbonyl)pyrrolidinyl]]-(1R)-[(tert-butyldiphenylsilyloxy)methyl]-2-(tert-butyloxycarbonyl)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: 68.0%

: 89813-47-8
N-(tert-butoxycarbonyl)-(2S,4R)-4-hydroxyproline benzyl ester

: 288582-53-6
O-(tert-butyldiphenylsilyl)-(2R)-amino-3-(tert-butyloxycarbonyl)aminopropanol

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

Guidance literature:: N-(tert-butoxycarbonyl)-(2S,4R)-4-hydroxyproline benzyl ester; With trifluoromethylsulfonic anhydride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at -30 ℃; for 1h;

O-(tert-butyldiphenylsilyl)-(2R)-amino-3-(tert-butyloxycarbonyl)aminopropanol; With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 ℃; for 72h; Further stages.;
DOI:10.1021/jo000071g

Reference yield:

: 24424-99-5
di-tert-butyl dicarbonate

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

Guidance literature:: Multi-step reaction with 4 steps

1.1: 91 percent / acetonitrile / 0 - 20 °C

2.1: 89 percent / DMAP; Et₃N / CH₂Cl₂ / 40 h / 20 °C

3.1: 88 percent / BF₃*OEt₂; AcOH / CH₂Cl₂ / 2 h / 0 °C

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

4.2: 68 percent / diisopropylethylamine / CH₂Cl₂ / 72 h / 0 °C

With dmap; trifluoromethylsulfonic anhydride; boron trifluoride diethyl etherate; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; In dichloromethane; acetonitrile; 1.1: Acylation / 2.1: silylation / 3.1: detritylation / 4.1: sulfonation / 4.2: Substitution;
DOI:10.1021/jo000071g

Reference yield:

: 288582-51-4
(2R)-triphenylmethylamino-3-(tert-butyloxycarbonyl)aminopropanol

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

Guidance literature:: Multi-step reaction with 3 steps

1.1: 89 percent / DMAP; Et₃N / CH₂Cl₂ / 40 h / 20 °C

2.1: 88 percent / BF₃*OEt₂; AcOH / CH₂Cl₂ / 2 h / 0 °C

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

3.2: 68 percent / diisopropylethylamine / CH₂Cl₂ / 72 h / 0 °C

With dmap; trifluoromethylsulfonic anhydride; boron trifluoride diethyl etherate; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; In dichloromethane; 1.1: silylation / 2.1: detritylation / 3.1: sulfonation / 3.2: Substitution;
DOI:10.1021/jo000071g