N-[(benzyloxycarbonyl)methyl]-N-[(2S,4S)-4-[2-(benzyloxycarbonyl)-N-[(benzyloxycarbonyl)methyl]pyrrolidinyl]]-(2R)-N,N-[bis[(benzyloxycarbonyl)methyl]amino]-3-hydroxy-O-[[N-(tert-butyloxycarbonyl)]aminoacetyl]propylamine

Base Information

Chemical Name:N-[(benzyloxycarbonyl)methyl]-N-[(2S,4S)-4-[2-(benzyloxycarbonyl)-N-[(benzyloxycarbonyl)methyl]pyrrolidinyl]]-(2R)-N,N-[bis[(benzyloxycarbonyl)methyl]amino]-3-hydroxy-O-[[N-(tert-butyloxycarbonyl)]aminoacetyl]propylamine
CAS No.:288582-59-2
Molecular Formula:C₅₈H₆₆N₄O₁₄
Molecular Weight:1043.18
Hs Code.:

N-[(benzyloxycarbonyl)methyl]-N-[(2S,4S)-4-[2-(benzyloxycarbonyl)-N-[(benzyloxycarbonyl)methyl]pyrrolidinyl]]-(2R)-N,N-[bis[(benzyloxycarbonyl)methyl]amino]-3-hydroxy-O-[[N-(tert-butyloxycarbonyl)]aminoacetyl]propylamine

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Chemical Property of N-[(benzyloxycarbonyl)methyl]-N-[(2S,4S)-4-[2-(benzyloxycarbonyl)-N-[(benzyloxycarbonyl)methyl]pyrrolidinyl]]-(2R)-N,N-[bis[(benzyloxycarbonyl)methyl]amino]-3-hydroxy-O-[[N-(tert-butyloxycarbonyl)]aminoacetyl]propylamine

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Technology Process of N-[(benzyloxycarbonyl)methyl]-N-[(2S,4S)-4-[2-(benzyloxycarbonyl)-N-[(benzyloxycarbonyl)methyl]pyrrolidinyl]]-(2R)-N,N-[bis[(benzyloxycarbonyl)methyl]amino]-3-hydroxy-O-[[N-(tert-butyloxycarbonyl)]aminoacetyl]propylamine

There total 6 articles about N-[(benzyloxycarbonyl)methyl]-N-[(2S,4S)-4-[2-(benzyloxycarbonyl)-N-[(benzyloxycarbonyl)methyl]pyrrolidinyl]]-(2R)-N,N-[bis[(benzyloxycarbonyl)methyl]amino]-3-hydroxy-O-[[N-(tert-butyloxycarbonyl)]aminoacetyl]propylamine 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:

: 4530-20-5
BOC-glycine

: 288582-46-7
N-[(benzyloxycarbonyl)methyl]-N-[(2S,4S)-4-[2-(benzyloxycarbonyl)-N-[(benzyloxycarbonyl)methyl]pyrrolidinyl]]-(2R)-N,N-[bis[(benzyloxycarbonyl)methyl]amino]-3-(tert-butyldiphenylsilyloxy)propylamine

: 288582-59-2
N-[(benzyloxycarbonyl)methyl]-N-[(2S,4S)-4-[2-(benzyloxycarbonyl)-N-[(benzyloxycarbonyl)methyl]pyrrolidinyl]]-(2R)-N,N-[bis[(benzyloxycarbonyl)methyl]amino]-3-hydroxy-O-[[N-(tert-butyloxycarbonyl)]aminoacetyl]propylamine

Guidance literature:: N-[(benzyloxycarbonyl)methyl]-N-[(2S,4S)-4-[2-(benzyloxycarbonyl)-N-[(benzyloxycarbonyl)methyl]pyrrolidinyl]]-(2R)-N,N-[bis[(benzyloxycarbonyl)methyl]amino]-3-(tert-butyldiphenylsilyloxy)propylamine; With pyridine hydrogenfluoride; In tetrahydrofuran; at 20 ℃; for 1.5h;

BOC-glycine; With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 0 - 20 ℃; Further stages.;
DOI:10.1021/jo000071g

Reference yield:

: 77902-89-7
benzyl <(trifluoromethyl)sulfonyloxy>acetate

: 288582-59-2
N-[(benzyloxycarbonyl)methyl]-N-[(2S,4S)-4-[2-(benzyloxycarbonyl)-N-[(benzyloxycarbonyl)methyl]pyrrolidinyl]]-(2R)-N,N-[bis[(benzyloxycarbonyl)methyl]amino]-3-hydroxy-O-[[N-(tert-butyloxycarbonyl)]aminoacetyl]propylamine

Guidance literature:: Multi-step reaction with 2 steps

1.1: 71 percent / diisopropylethylamine / CH₂Cl₂ / -78 - -10 °C

2.1: pyridine*HF / tetrahydrofuran / 1.5 h / 20 °C

2.2: 477 mg / DCC; DMAP / CH₂Cl₂ / 0 - 20 °C

With pyridine hydrogenfluoride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; 1.1: Alkylation / 2.1: desilylation / 2.2: Condensation;
DOI:10.1021/jo000071g

Reference yield:

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

: 288582-59-2
N-[(benzyloxycarbonyl)methyl]-N-[(2S,4S)-4-[2-(benzyloxycarbonyl)-N-[(benzyloxycarbonyl)methyl]pyrrolidinyl]]-(2R)-N,N-[bis[(benzyloxycarbonyl)methyl]amino]-3-hydroxy-O-[[N-(tert-butyloxycarbonyl)]aminoacetyl]propylamine

Guidance literature:: Multi-step reaction with 5 steps

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

1.2: 65 percent / diisopropylethylamine / CH₂Cl₂ / 76 h / -10 °C

2.1: 91 percent / Et₃N; DMAP / CH₂Cl₂ / 1 h / 20 °C

3.1: CF₃COOH; Et₃SiH / CH₂Cl₂ / 1 h / 20 °C

4.1: 71 percent / diisopropylethylamine / CH₂Cl₂ / -78 - -10 °C

5.1: pyridine*HF / tetrahydrofuran / 1.5 h / 20 °C

5.2: 477 mg / DCC; DMAP / CH₂Cl₂ / 0 - 20 °C

With triethylsilane; dmap; trifluoromethylsulfonic anhydride; pyridine hydrogenfluoride; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; 1.1: sulfonation / 1.2: Substitution / 2.1: silylation / 3.1: carbamate cleavage; hydrogenolysis / 4.1: Alkylation / 5.1: desilylation / 5.2: Condensation;
DOI:10.1021/jo000071g