(S)-3-((tert-butoxycarbonyl)amino)-2-((tert-butyldiphenylsilyl)oxy)propanoic acid

Base Information

• Chemical Name: (S)-3-((tert-butoxycarbonyl)amino)-2-((tert-butyldiphenylsilyl)oxy)propanoic acid
• CAS No.: 1392222-60-4
• Molecular Formula: C₂₄H₃₃NO₅Si
• Molecular Weight: 443.615
• Mol file: 1392222-60-4.mol

Synonyms:(S)-3-((tert-butoxycarbonyl)amino)-2-((tert-butyldiphenylsilyl)oxy)propanoic acid

Chemical Property of (S)-3-((tert-butoxycarbonyl)amino)-2-((tert-butyldiphenylsilyl)oxy)propanoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-3-((tert-butoxycarbonyl)amino)-2-((tert-butyldiphenylsilyl)oxy)propanoic acid

There total 4 articles about (S)-3-((tert-butoxycarbonyl)amino)-2-((tert-butyldiphenylsilyl)oxy)propanoic 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: 94.0%

methyl (S)-3-((tert-butoxycarbonyl)amino)-2-((tert-butyldiphenylsilyl)oxy)propanoate (1159016-08-6) → (S)-3-((tert-butoxycarbonyl)amino)-2-((tert-butyldiphenylsilyl)oxy)propanoic acid (1392222-60-4)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; methanol; at 0 - 20 ℃; for 16h; Inert atmosphere; Schlenk technique;

DOI:10.1021/acs.orglett.8b01756

Reference yield:

(2S)‐3‐{[(tert‐butoxy)carbonyl]amino}‐2‐hydroxypropanoic acid methyl ester (133153-76-1) → (S)-3-((tert-butoxycarbonyl)amino)-2-((tert-butyldiphenylsilyl)oxy)propanoic acid (1392222-60-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 1H-imidazole; dmap / dichloromethane / Inert atmosphere

2: sodium hydroxide / tetrahydrofuran; methanol; water / 20 °C / Cooling with ice; Inert atmosphere

With 1H-imidazole; dmap; sodium hydroxide; In tetrahydrofuran; methanol; dichloromethane; water;

DOI:10.1021/ol300576n

Reference yield:

methyl (5S)-3-tert-butoxycarbonyloxazolidin-2-one-5-carboxylate → (S)-3-((tert-butoxycarbonyl)amino)-2-((tert-butyldiphenylsilyl)oxy)propanoic acid (1392222-60-4)

Guidance literature:

Multi-step reaction with 3 steps

1: caesium carbonate / methanol / 1 h / 20 °C / Inert atmosphere

2: 1H-imidazole; dmap / dichloromethane / Inert atmosphere

3: sodium hydroxide / tetrahydrofuran; methanol; water / 20 °C / Cooling with ice; Inert atmosphere

With 1H-imidazole; dmap; caesium carbonate; sodium hydroxide; In tetrahydrofuran; methanol; dichloromethane; water;

DOI:10.1021/ol300576n

upstream raw materials:

(2S)‐3‐{[(tert‐butoxy)carbonyl]amino}‐2‐hydroxypropanoic acid methyl ester

methyl (S)-3-((tert-butoxycarbonyl)amino)-2-((tert-butyldiphenylsilyl)oxy)propanoate

tert-butylchlorodiphenylsilane

Downstream raw materials:

Boc-Ise(TBDPS)-Trp(5-Br)-OMe

Boc-Ise(TBDPS)-Trp(5-Br)-OH

C₅₆H₆₅BrCl₄N₈O₁₃Si

C₄₀H₄₇BrCl₄N₈O₁₃