dimethyl (-)-(2S,2'S,3aS,3'aS,8aS,8'aS)-1,1'-bis{(S)-2-[tert-butoxycarbonyl(methyl)amino]-3-phenylpropanoyl}-2,2',3,3',8,8a,8',8'a-octahydro-1H,1'H-3a,3'a-bipyrrolo[2,3-b]indole-2,2-dicarboxylate

Base Information

• Chemical Name: dimethyl (-)-(2S,2'S,3aS,3'aS,8aS,8'aS)-1,1'-bis{(S)-2-[tert-butoxycarbonyl(methyl)amino]-3-phenylpropanoyl}-2,2',3,3',8,8a,8',8'a-octahydro-1H,1'H-3a,3'a-bipyrrolo[2,3-b]indole-2,2-dicarboxylate
• CAS No.: 1629094-38-7
• Molecular Formula: C₅₄H₆₄N₆O₁₀
• Molecular Weight: 957.136
• Mol file: 1629094-38-7.mol

Synonyms:dimethyl (-)-(2S,2'S,3aS,3'aS,8aS,8'aS)-1,1'-bis{(S)-2-[tert-butoxycarbonyl(methyl)amino]-3-phenylpropanoyl}-2,2',3,3',8,8a,8',8'a-octahydro-1H,1'H-3a,3'a-bipyrrolo[2,3-b]indole-2,2-dicarboxylate

Chemical Property of dimethyl (-)-(2S,2'S,3aS,3'aS,8aS,8'aS)-1,1'-bis{(S)-2-[tert-butoxycarbonyl(methyl)amino]-3-phenylpropanoyl}-2,2',3,3',8,8a,8',8'a-octahydro-1H,1'H-3a,3'a-bipyrrolo[2,3-b]indole-2,2-dicarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of dimethyl (-)-(2S,2'S,3aS,3'aS,8aS,8'aS)-1,1'-bis{(S)-2-[tert-butoxycarbonyl(methyl)amino]-3-phenylpropanoyl}-2,2',3,3',8,8a,8',8'a-octahydro-1H,1'H-3a,3'a-bipyrrolo[2,3-b]indole-2,2-dicarboxylate

There total 6 articles about dimethyl (-)-(2S,2'S,3aS,3'aS,8aS,8'aS)-1,1'-bis{(S)-2-[tert-butoxycarbonyl(methyl)amino]-3-phenylpropanoyl}-2,2',3,3',8,8a,8',8'a-octahydro-1H,1'H-3a,3'a-bipyrrolo[2,3-b]indole-2,2-dicarboxylate 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: 36.0%

Boc-N-Me-Phe-OH (37553-65-4) + dimethyl (-)-(2S,2'S,3aS,3'aS,8aR,8'aR)-2,2',3,3',8,8a,8',8'a-octahydro-1H,1'H-3a,3'a-bipyrrolo[2,3-b]indole-2,2'-dicarboxylate (1629094-37-6) → dimethyl (-)-(2S,2'S,3aS,3'aS,8aS,8'aS)-1,1'-bis{(S)-2-[tert-butoxycarbonyl(methyl)amino]-3-phenylpropanoyl}-2,2',3,3',8,8a,8',8'a-octahydro-1H,1'H-3a,3'a-bipyrrolo[2,3-b]indole-2,2-dicarboxylate (1629094-38-7)

Guidance literature:

Boc-N-Me-Phe-OH; dimethyl (-)-(2S,2'S,3aS,3'aS,8aR,8'aR)-2,2',3,3',8,8a,8',8'a-octahydro-1H,1'H-3a,3'a-bipyrrolo[2,3-b]indole-2,2'-dicarboxylate; With triethylamine; In N,N-dimethyl-formamide; at 0 ℃; for 0.166667h;

With N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 0 ℃; for 80h;

DOI:10.1055/s-0033-1339126

Reference yield:

L-Tryptophan (73-22-3,27732-43-0,80206-30-0,27813-82-7) → dimethyl (-)-(2S,2'S,3aS,3'aS,8aS,8'aS)-1,1'-bis{(S)-2-[tert-butoxycarbonyl(methyl)amino]-3-phenylpropanoyl}-2,2',3,3',8,8a,8',8'a-octahydro-1H,1'H-3a,3'a-bipyrrolo[2,3-b]indole-2,2-dicarboxylate (1629094-38-7)

Guidance literature:

Multi-step reaction with 6 steps

1.1: acetyl chloride / 0 - 50 °C

2.1: sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate / dichloromethane / 24 h / 0 - 20 °C

3.1: N-Bromosuccinimide; pyridinium p-toluenesulfonate / dichloromethane / 0 °C

4.1: zinc; nickel(II) iodide; 1,10-Phenanthroline / pyridine; N,N-dimethyl acetamide / 24 h / 25 °C

5.1: trimethylsilyl iodide / acetonitrile / 0.58 h / 0 - 20 °C

6.1: triethylamine / N,N-dimethyl-formamide / 0.17 h / 0 °C

6.2: 80 h / 0 °C

With nickel(II) iodide; N-Bromosuccinimide; 1,10-Phenanthroline; trimethylsilyl iodide; tetra(n-butyl)ammonium hydrogensulfate; pyridinium p-toluenesulfonate; triethylamine; acetyl chloride; sodium hydroxide; zinc; In pyridine; dichloromethane; N,N-dimethyl acetamide; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1055/s-0033-1339126

Reference yield:

L-tryptophan methyl ester (4299-70-1) → dimethyl (-)-(2S,2'S,3aS,3'aS,8aS,8'aS)-1,1'-bis{(S)-2-[tert-butoxycarbonyl(methyl)amino]-3-phenylpropanoyl}-2,2',3,3',8,8a,8',8'a-octahydro-1H,1'H-3a,3'a-bipyrrolo[2,3-b]indole-2,2-dicarboxylate (1629094-38-7)

Guidance literature:

Multi-step reaction with 5 steps

1.1: sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate / dichloromethane / 24 h / 0 - 20 °C

2.1: N-Bromosuccinimide; pyridinium p-toluenesulfonate / dichloromethane / 0 °C

3.1: zinc; nickel(II) iodide; 1,10-Phenanthroline / pyridine; N,N-dimethyl acetamide / 24 h / 25 °C

4.1: trimethylsilyl iodide / acetonitrile / 0.58 h / 0 - 20 °C

5.1: triethylamine / N,N-dimethyl-formamide / 0.17 h / 0 °C

5.2: 80 h / 0 °C

With nickel(II) iodide; N-Bromosuccinimide; 1,10-Phenanthroline; trimethylsilyl iodide; tetra(n-butyl)ammonium hydrogensulfate; pyridinium p-toluenesulfonate; triethylamine; sodium hydroxide; zinc; In pyridine; dichloromethane; N,N-dimethyl acetamide; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1055/s-0033-1339126

upstream raw materials:

L-Tryptophan

L-tryptophan methyl ester

methyl (2S,3aR,8aR)-[3a-bromo-(1,2,3,3a,8,8a)-hexahydropyrrolo[2,3-b]indole-1,8-di-tertbutoxycarbonyl]-2-carboxylate

Boc-N-Me-Phe-OH

Downstream raw materials:

(-)-ditryptophenaline