(Z)-2-bromo-5-{tert-butoxycarbonyl-[5-(tert-butyldiphenylsilanyloxy)pentyl]amino}pent-2-enoic acid methyl ester

Base Information

• Chemical Name: (Z)-2-bromo-5-{tert-butoxycarbonyl-[5-(tert-butyldiphenylsilanyloxy)pentyl]amino}pent-2-enoic acid methyl ester
• CAS No.: 221136-02-3
• Molecular Formula: C₃₂H₄₆BrNO₅Si
• Molecular Weight: 632.71
• Mol file: 221136-02-3.mol

Synonyms:(Z)-2-bromo-5-{tert-butoxycarbonyl-[5-(tert-butyldiphenylsilanyloxy)pentyl]amino}pent-2-enoic acid methyl ester

Chemical Property of (Z)-2-bromo-5-{tert-butoxycarbonyl-[5-(tert-butyldiphenylsilanyloxy)pentyl]amino}pent-2-enoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z)-2-bromo-5-{tert-butoxycarbonyl-[5-(tert-butyldiphenylsilanyloxy)pentyl]amino}pent-2-enoic acid methyl ester

There total 6 articles about (Z)-2-bromo-5-{tert-butoxycarbonyl-[5-(tert-butyldiphenylsilanyloxy)pentyl]amino}pent-2-enoic 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: 91.0%

[5-(tert-butyldiphenylsilanyloxy)pentyl](3-oxopropyl)carbamic acid tert-butyl ester (221135-97-3) + methyl 2-bromo-2-(triphenylphosphanylidene)acetate (13504-77-3) → 2-bromo-5-{tert-butoxycarbonyl-[5-(tert-butyl-diphenyl-silanyloxy)-pentyl]-amino}-pent-2-enoic acid methyl ester + (Z)-2-bromo-5-{tert-butoxycarbonyl-[5-(tert-butyldiphenylsilanyloxy)pentyl]amino}pent-2-enoic acid methyl ester (221136-02-3)

Guidance literature:

In dichloromethane;

DOI:10.1021/ja9829259

Reference yield:

5-hydroxypentylamine (2508-29-4) → (Z)-2-bromo-5-{tert-butoxycarbonyl-[5-(tert-butyldiphenylsilanyloxy)pentyl]amino}pent-2-enoic acid methyl ester (221136-02-3)

Guidance literature:

Multi-step reaction with 4 steps

1: Na₃CO₃ / H₂O; dioxane / 14 h / 20 °C

2: imidazole / dimethylformamide / 14 h / 20 °C

3: 72 percent / camphorsulfonic acid / CH₂Cl₂ / 0.75 h / 0 - 20 °C

4: 91 percent / CH₂Cl₂ / 22 h / 20 °C

With 1H-imidazole; camphor-10-sulfonic acid; sodium carbonate; In 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide; 4: Wittig reaction;

DOI:10.1021/ja0202964

Reference yield:

N-(tert-butyloxycarbonyl)-5-aminopentanol (75178-90-4) → (Z)-2-bromo-5-{tert-butoxycarbonyl-[5-(tert-butyldiphenylsilanyloxy)pentyl]amino}pent-2-enoic acid methyl ester (221136-02-3)

Guidance literature:

Multi-step reaction with 3 steps

1: imidazole / dimethylformamide / 14 h / 20 °C

2: 72 percent / camphorsulfonic acid / CH₂Cl₂ / 0.75 h / 0 - 20 °C

3: 91 percent / CH₂Cl₂ / 22 h / 20 °C

With 1H-imidazole; camphor-10-sulfonic acid; In dichloromethane; N,N-dimethyl-formamide; 3: Wittig reaction;

DOI:10.1021/ja0202964

upstream raw materials:

[5-(tert-butyldiphenylsilanyloxy)pentyl](3-oxopropyl)carbamic acid tert-butyl ester

methyl 2-bromo-2-(triphenylphosphanylidene)acetate

5-hydroxypentylamine

di-tert-butyl dicarbonate

Downstream raw materials:

2-bromo-5-[5-(tert-butyl-diphenyl-silanyloxy)-pentylamino]-pent-2-enoic acid methyl ester