ethyl (S)-2-((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-((tert-butoxycarbonyl)amino)-3-(2-4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl-4,5-dimethoxyphenyl)propanoate
• CAS No.: 1644527-04-7
• Molecular Formula: C₂₄H₃₈BNO₈
• Molecular Weight: 479.379
• Mol file: 1644527-04-7.mol

Synonyms:ethyl (S)-2-((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-((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-((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-((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: 62.0%

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-((tert-butoxycarbonyl)amino)-3-(2-4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl-4,5-dimethoxyphenyl)propanoate (1644527-04-7)

Guidance literature:

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate; In N,N-dimethyl-formamide; at 80 ℃; 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-((tert-butoxycarbonyl)amino)-3-(2-4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl-4,5-dimethoxyphenyl)propanoate (1644527-04-7) + ethyl (R)-2-((tert-butoxycarbonyl)amino)-3-(2-4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl-4,5-dimethoxyphenyl)propanoate

Guidance literature:

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate; In N,N-dimethyl-formamide; at 80 ℃; for 18h; Overall yield = 62 %; Overall yield = 740 mg; Inert atmosphere;

DOI:10.1039/c6cc03295h

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

upstream raw materials:

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

bis(pinacol)diborane

Downstream raw materials:

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

C₂₃H₃₄⁽¹⁸⁾FNO₈