ethyl (S)-2-((di-tert-butoxycarbonyl)amino)-3-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4,5-dimethoxyphenyl)propanoate

Base Information

• Chemical Name: ethyl (S)-2-((di-tert-butoxycarbonyl)amino)-3-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4,5-dimethoxyphenyl)propanoate
• CAS No.: 1644527-05-8
• Molecular Formula: C₂₉H₄₆BNO₁₀
• Molecular Weight: 579.496
• Mol file: 1644527-05-8.mol

Synonyms:ethyl (S)-2-((di-tert-butoxycarbonyl)amino)-3-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4,5-dimethoxyphenyl)propanoate

Chemical Property of ethyl (S)-2-((di-tert-butoxycarbonyl)amino)-3-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4,5-dimethoxyphenyl)propanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl (S)-2-((di-tert-butoxycarbonyl)amino)-3-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4,5-dimethoxyphenyl)propanoate

There total 2 articles about ethyl (S)-2-((di-tert-butoxycarbonyl)amino)-3-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4,5-dimethoxyphenyl)propanoate 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: 53.0%

di-tert-butyl dicarbonate (24424-99-5) + ethyl (S)-2-((tert-butoxycarbonyl)amino)-3-(2-4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl-4,5-dimethoxyphenyl)propanoate (1644527-04-7) → ethyl (S)-2-((di-tert-butoxycarbonyl)amino)-3-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4,5-dimethoxyphenyl)propanoate (1644527-05-8)

Guidance literature:

With dmap; triethylamine; In acetonitrile; at 20 ℃; for 18h; Inert atmosphere;

DOI:10.1002/anie.201404436

Reference yield:

ethyl (S)-2-((tert-butoxycarbonyl)amino)-3-(2-iodo-4,5-dimethoxyphenyl)propanoate (1421282-25-8) + bis(pinacol)diborane (73183-34-3) → ethyl (S)-2-((di-tert-butoxycarbonyl)amino)-3-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4,5-dimethoxyphenyl)propanoate (1644527-05-8)

Guidance literature:

Multi-step reaction with 2 steps

1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate / N,N-dimethyl-formamide / 18 h / 80 °C / Inert atmosphere

2: dmap; triethylamine / acetonitrile / 18 h / 20 °C / Inert atmosphere

With dmap; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate; triethylamine; In N,N-dimethyl-formamide; acetonitrile;

DOI:10.1002/anie.201404436

Reference yield:

ethyl (S)-2-((di-tert-butoxycarbonyl)amino)-3-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4,5-dimethoxyphenyl)propanoate (1644527-05-8) → C23H34(18)FNO8 (1644527-25-2)

Guidance literature:

With [¹⁸F]-potassium fluoride; tetrakis(pyridine)copper(II) bis(trifluoromethanesulfonate); [2.2.2]cryptande; In N,N-dimethyl-formamide; acetonitrile; at 110 ℃; for 0.333333h; Reagent/catalyst;

DOI:10.1002/anie.201404436

upstream raw materials:

di-tert-butyl dicarbonate

ethyl (S)-2-((tert-butoxycarbonyl)amino)-3-(2-4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl-4,5-dimethoxyphenyl)propanoate

ethyl (S)-2-((tert-butoxycarbonyl)amino)-3-(2-iodo-4,5-dimethoxyphenyl)propanoate

bis(pinacol)diborane

Downstream raw materials:

C₂₃H₃₄⁽¹⁸⁾FNO₈