2-benzyloxycarbonylamino-3-[3-bromo-5-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-phenyl]-propionic acid methyl ester

Base Information

• Chemical Name: 2-benzyloxycarbonylamino-3-[3-bromo-5-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-phenyl]-propionic acid methyl ester
• CAS No.: 579469-96-8
• Molecular Formula: C₂₅H₃₄BrNO₆Si
• Molecular Weight: 552.538
• Mol file: 579469-96-8.mol

Synonyms:2-benzyloxycarbonylamino-3-[3-bromo-5-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-phenyl]-propionic acid methyl ester

Chemical Property of 2-benzyloxycarbonylamino-3-[3-bromo-5-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-phenyl]-propionic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-benzyloxycarbonylamino-3-[3-bromo-5-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-phenyl]-propionic acid methyl ester

There total 4 articles about 2-benzyloxycarbonylamino-3-[3-bromo-5-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-phenyl]-propionic acid methyl 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:

L-3-(3-acetyl-4-hydroxyphenyl)-N-(benzyloxycarbonyl)alanine methyl ester (110774-03-3) → 2-benzyloxycarbonylamino-3-[3-bromo-5-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-phenyl]-propionic acid methyl ester (579469-96-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 99 percent / N-bromosuccinimide / acetonitrile / 18 h / 25 °C

2: 94 percent / K₂CO₃ / dimethylformamide / 5 h / 25 °C

3: 61 percent / trifluoroperacetic acid / CH₂Cl₂ / 48 h / Heating

4: 97 percent / HCl / dioxane / 2 h / 25 °C

5: 81 percent / lutidine / tetrahydrofuran / 4 h / 25 °C

With hydrogenchloride; N-Bromosuccinimide; trifluoroacetyl peroxide; lutidine; potassium carbonate; In tetrahydrofuran; 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 3: Baeyer-Villiger oxidation;

DOI:10.1016/S0040-4039(03)00856-6

Reference yield:

(S)-3-(3-Acetoxy-5-bromo-4-methoxy-phenyl)-2-benzyloxycarbonylamino-propionic acid methyl ester (579469-94-6) → 2-benzyloxycarbonylamino-3-[3-bromo-5-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-phenyl]-propionic acid methyl ester (579469-96-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 97 percent / HCl / dioxane / 2 h / 25 °C

2: 81 percent / lutidine / tetrahydrofuran / 4 h / 25 °C

With hydrogenchloride; lutidine; In tetrahydrofuran; 1,4-dioxane;

DOI:10.1016/S0040-4039(03)00856-6

Reference yield:

(S)-3-(3-Acetyl-5-bromo-4-methoxy-phenyl)-2-benzyloxycarbonylamino-propionic acid methyl ester (412351-03-2) → 2-benzyloxycarbonylamino-3-[3-bromo-5-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-phenyl]-propionic acid methyl ester (579469-96-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 61 percent / trifluoroperacetic acid / CH₂Cl₂ / 48 h / Heating

2: 97 percent / HCl / dioxane / 2 h / 25 °C

3: 81 percent / lutidine / tetrahydrofuran / 4 h / 25 °C

With hydrogenchloride; trifluoroacetyl peroxide; lutidine; In tetrahydrofuran; 1,4-dioxane; dichloromethane; 1: Baeyer-Villiger oxidation;

DOI:10.1016/S0040-4039(03)00856-6

upstream raw materials:

L-3-(3-acetyl-4-hydroxyphenyl)-N-(benzyloxycarbonyl)alanine methyl ester

(S)-3-(3-Acetyl-5-bromo-4-methoxy-phenyl)-2-benzyloxycarbonylamino-propionic acid methyl ester

(S)-3-(3-Acetyl-5-bromo-4-hydroxy-phenyl)-2-benzyloxycarbonylamino-propionic acid methyl ester

(S)-3-(3-Acetoxy-5-bromo-4-methoxy-phenyl)-2-benzyloxycarbonylamino-propionic acid methyl ester

Downstream raw materials:

(2S,3S)-2-{(S)-3-[5'-((S)-2-Benzyloxycarbonylamino-2-methoxycarbonyl-ethyl)-3'-(tert-butyl-dimethyl-silanyloxy)-6,2'-dimethoxy-biphenyl-3-yl]-2-tert-butoxycarbonylamino-propionylamino}-3-methyl-pentanoic acid benzyl ester

(S)-2-((2S,3S)-2-Benzyloxycarbonylamino-3-methyl-pentanoylamino)-3-[5'-((S)-2-tert-butoxycarbonylamino-3-methoxymethoxy-propyl)-5-(tert-butyl-dimethyl-silanyloxy)-6,2'-dimethoxy-biphenyl-3-yl]-propionic acid methyl ester

(S)-3-[5'-[(S)-2-((2S,3S)-2-Benzyloxycarbonylamino-3-methyl-pentanoylamino)-2-methoxycarbonyl-ethyl]-3'-(tert-butyl-dimethyl-silanyloxy)-6,2'-dimethoxy-biphenyl-3-yl]-2-tert-butoxycarbonylamino-propionic acid

(S)-2-((2S,3S)-2-Benzyloxycarbonylamino-3-methyl-pentanoylamino)-3-[5'-((S)-2-tert-butoxycarbonylamino-3-hydroxy-propyl)-5-(tert-butyl-dimethyl-silanyloxy)-6,2'-dimethoxy-biphenyl-3-yl]-propionic acid methyl ester