N-tert-butyoxycarbonyl-N-methyl-2-bromo-(R)-tryptophanyl-O-tert-butyldimethylsilyl-(R)-β-tyrosine tert-butyl ester

Base Information

• Chemical Name: N-tert-butyoxycarbonyl-N-methyl-2-bromo-(R)-tryptophanyl-O-tert-butyldimethylsilyl-(R)-β-tyrosine tert-butyl ester
• CAS No.: 112896-94-3
• Molecular Formula: C₃₆H₅₂BrN₃O₆Si
• Molecular Weight: 730.815
• Mol file: 112896-94-3.mol

Synonyms:N-tert-butyoxycarbonyl-N-methyl-2-bromo-(R)-tryptophanyl-O-tert-butyldimethylsilyl-(R)-β-tyrosine tert-butyl ester

Chemical Property of N-tert-butyoxycarbonyl-N-methyl-2-bromo-(R)-tryptophanyl-O-tert-butyldimethylsilyl-(R)-β-tyrosine tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-tert-butyoxycarbonyl-N-methyl-2-bromo-(R)-tryptophanyl-O-tert-butyldimethylsilyl-(R)-β-tyrosine tert-butyl ester

There total 10 articles about N-tert-butyoxycarbonyl-N-methyl-2-bromo-(R)-tryptophanyl-O-tert-butyldimethylsilyl-(R)-β-tyrosine tert-butyl ester 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: 94.0%

N-tert-butoxycarbonyl-N-methyl-2-bromo-(R)-tryptophan (112896-89-6) + O-tert-butyldimethylsilyl-(R)-β-tyrosine tert-but (112896-93-2) → N-tert-butyoxycarbonyl-N-methyl-2-bromo-(R)-tryptophanyl-O-tert-butyldimethylsilyl-(R)-β-tyrosine tert-butyl ester (112896-94-3)

Guidance literature:

With 1-hydroxybenzotriazol-hydrate; dicyclohexyl-carbodiimide; In tetrahydrofuran; at 0 ℃; for 5h;

DOI:10.3987/COM-94-S(B)52

Reference yield:

N-tert-butyloxycarbonyl-L-4-hydroxyphenylglycine (69651-48-5) → N-tert-butyoxycarbonyl-N-methyl-2-bromo-(R)-tryptophanyl-O-tert-butyldimethylsilyl-(R)-β-tyrosine tert-butyl ester (112896-94-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 77 percent / imidazole / dimethylformamide / 9 h / Ambient temperature

2: 1.) ClCO₂Et, Et₃N / 1.) ether, 0 deg C, 1 h, 2.) ether, RT, 7 h

3: 50 percent / silver benzoate, Et₃N / 0.05 h / 80 °C

4: 60 percent / 2,6-lutidine, tert-butyldimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / 3 h / 0 °C

5: 94 percent / 1-hydroxybenzotriazole hydrate, DCC / tetrahydrofuran / 5 h / 0 °C

With 1H-imidazole; 2,6-dimethylpyridine; t-butyldimethylsiyl triflate; silver benzoate; chloroformic acid ethyl ester; 1-hydroxybenzotriazol-hydrate; triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.3987/COM-94-S(B)52

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → N-tert-butyoxycarbonyl-N-methyl-2-bromo-(R)-tryptophanyl-O-tert-butyldimethylsilyl-(R)-β-tyrosine tert-butyl ester (112896-94-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 77 percent / imidazole / dimethylformamide / 9 h / Ambient temperature

2: 1.) ClCO₂Et, Et₃N / 1.) ether, 0 deg C, 1 h, 2.) ether, RT, 7 h

3: 50 percent / silver benzoate, Et₃N / 0.05 h / 80 °C

4: 60 percent / 2,6-lutidine, tert-butyldimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / 3 h / 0 °C

5: 94 percent / 1-hydroxybenzotriazole hydrate, DCC / tetrahydrofuran / 5 h / 0 °C

With 1H-imidazole; 2,6-dimethylpyridine; t-butyldimethylsiyl triflate; silver benzoate; chloroformic acid ethyl ester; 1-hydroxybenzotriazol-hydrate; triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.3987/COM-94-S(B)52

upstream raw materials:

N-tert-butoxycarbonyl-N-methyl-2-bromo-(R)-tryptophan

O-tert-butyldimethylsilyl-(R)-β-tyrosine tert-but

N-tert-butyloxycarbonyl-L-4-hydroxyphenylglycine

(S)-hydroxyphenylglycine

Downstream raw materials:

N-methyl-2-bromo-(R)-tryptophanyl-O-tert-butyldimethylsilyl-(R)-β-tyrosine tert-butyl ester

jasplakinolide

(S)-alanyl-N-methyl-2-bromo-(R)-tryptophanyl-O-tert-butyldimethylsilyl-(R)-β-tyrosine tert-butyl ester

N-tert-butoxycarbonyl-(S)-alanyl-N-methyl-2-bromo-(R)-tryptophanyl-O-tert-butyldimethylsilyl-(R)-β-tyrosine tert-butyl ester