(S)-2-((tert-butoxycarbonyl)amino)-5-((tert-butyldiphenylsilyl)oxy)pentanoic acid

Base Information

• Chemical Name: (S)-2-((tert-butoxycarbonyl)amino)-5-((tert-butyldiphenylsilyl)oxy)pentanoic acid
• CAS No.: 1073554-62-7
• Molecular Formula: C₂₆H₃₇NO₅Si
• Molecular Weight: 471.669
• Mol file: 1073554-62-7.mol

Synonyms:(S)-2-((tert-butoxycarbonyl)amino)-5-((tert-butyldiphenylsilyl)oxy)pentanoic acid

Chemical Property of (S)-2-((tert-butoxycarbonyl)amino)-5-((tert-butyldiphenylsilyl)oxy)pentanoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-((tert-butoxycarbonyl)amino)-5-((tert-butyldiphenylsilyl)oxy)pentanoic acid

There total 8 articles about (S)-2-((tert-butoxycarbonyl)amino)-5-((tert-butyldiphenylsilyl)oxy)pentanoic acid 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: 63.0%

methyl (S)-2-(tert-butoxycarbonyl)amino-5-[tert-butyl(diphenyl)silanyloxy]pentanoate → (S)-2-((tert-butoxycarbonyl)amino)-5-((tert-butyldiphenylsilyl)oxy)pentanoic acid (1073554-62-7)

Guidance literature:

With lithium hydroxide; In water; at 0 - 20 ℃; for 3h;

DOI:10.1021/acs.jnatprod.0c00921

Reference yield:

(S)-benzyl 2-((tert-butoxycarbonyl)amino)5-((tert-butyldiphenylsilyl)oxy)pentanoate (1073554-61-6) → (S)-2-((tert-butoxycarbonyl)amino)-5-((tert-butyldiphenylsilyl)oxy)pentanoic acid (1073554-62-7)

Guidance literature:

With hydrogen; palladium 10% on activated carbon; In ethyl acetate; for 16h; under 2250.23 Torr;

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → (S)-2-((tert-butoxycarbonyl)amino)-5-((tert-butyldiphenylsilyl)oxy)pentanoic acid (1073554-62-7)

Guidance literature:

Multi-step reaction with 5 steps

1.1: chloro-trimethyl-silane / Inert atmosphere

1.2: Inert atmosphere

1.3: Inert atmosphere

2.1: diisobutylaluminium hydride / tetrahydrofuran; hexane / 1 h / 1 - 40 °C / Inert atmosphere

3.1: 1H-imidazole / N,N-dimethyl-formamide / 20 °C / Inert atmosphere

4.1: lithium bromide / acetonitrile / Inert atmosphere

5.1: lithium hydroxide / water / 3 h / 0 - 20 °C

With 1H-imidazole; chloro-trimethyl-silane; diisobutylaluminium hydride; lithium bromide; lithium hydroxide; In tetrahydrofuran; hexane; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/acs.jnatprod.0c00921

upstream raw materials:

(S)-benzyl 2-((tert-butoxycarbonyl)amino)5-((tert-butyldiphenylsilyl)oxy)pentanoate

L-glutamic acid

di-tert-butyl dicarbonate

(S)-dimethyl 2-(bis(tert-butoxycarbonyl)amino)pentanedioate

Downstream raw materials:

4-[(S)-2-tert-butoxycarbonylamino-5-(tert-butyl-diphenyl-silanyloxy)-pentanoyl]-piperazine-1-carboxylic acid butyl ester