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

Base Information

Chemical Name:N-methyl-2-bromo-(R)-tryptophanyl-O-tert-butyldimethylsilyl-(R)-β-tyrosine tert-butyl ester
CAS No.:112896-83-0
Molecular Formula:C₃₁H₄₄BrN₃O₄Si
Molecular Weight:630.698
Hs Code.:

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

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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

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

There total 12 articles about 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: 82.0%

: 112896-94-3
N-tert-butyoxycarbonyl-N-methyl-2-bromo-(R)-tryptophanyl-O-tert-butyldimethylsilyl-(R)-β-tyrosine tert-butyl ester

: 112896-83-0
N-methyl-2-bromo-(R)-tryptophanyl-O-tert-butyldimethylsilyl-(R)-β-tyrosine tert-butyl ester

Guidance literature:: With 2,6-dimethylpyridine; t-butyldimethylsiyl triflate; In dichloromethane; for 2h; Ambient temperature;
DOI:10.3987/COM-94-S(B)52

Reference yield:

: 69651-48-5
N-tert-butyloxycarbonyl-L-4-hydroxyphenylglycine

: 112896-83-0
N-methyl-2-bromo-(R)-tryptophanyl-O-tert-butyldimethylsilyl-(R)-β-tyrosine tert-butyl ester

Guidance literature:: Multi-step reaction with 6 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

6: 82 percent / 2,6-lutidine, TBSOTf / CH₂Cl₂ / 2 h / Ambient temperature

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:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 112896-83-0
N-methyl-2-bromo-(R)-tryptophanyl-O-tert-butyldimethylsilyl-(R)-β-tyrosine tert-butyl ester

Guidance literature:: Multi-step reaction with 6 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

6: 82 percent / 2,6-lutidine, TBSOTf / CH₂Cl₂ / 2 h / Ambient temperature

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