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

Base Information

• Chemical Name: methyl (S)-3-((tert-butoxycarbonyl)amino)-2-((tert-butyldiphenylsilyl)oxy)propanoate
• CAS No.: 1159016-08-6
• Molecular Formula: C₂₅H₃₅NO₅Si
• Molecular Weight: 457.642
• Mol file: 1159016-08-6.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 2 articles about methyl (S)-3-((tert-butoxycarbonyl)amino)-2-((tert-butyldiphenylsilyl)oxy)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: 92.0%

(2S)‐3‐{[(tert‐butoxy)carbonyl]amino}‐2‐hydroxypropanoic acid methyl ester (133153-76-1) + tert-butylchlorodiphenylsilane (58479-61-1) → methyl (S)-3-((tert-butoxycarbonyl)amino)-2-((tert-butyldiphenylsilyl)oxy)propanoate (1159016-08-6)

Guidance literature:

With 1H-imidazole; dmap; In dichloromethane; at 20 ℃; for 16h; Inert atmosphere; Schlenk technique;

DOI:10.1021/acs.orglett.8b01756

Reference yield:

methyl (5S)-3-tert-butoxycarbonyloxazolidin-2-one-5-carboxylate → methyl (S)-3-((tert-butoxycarbonyl)amino)-2-((tert-butyldiphenylsilyl)oxy)propanoate (1159016-08-6)

Guidance literature:

Multi-step reaction with 2 steps

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

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

With 1H-imidazole; dmap; caesium carbonate; In methanol; dichloromethane;

DOI:10.1021/ol300576n

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

upstream raw materials:

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

tert-butylchlorodiphenylsilane

Downstream raw materials:

C₂₇H₃₇NO₅Si

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

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

C₅₆H₆₅BrCl₄N₈O₁₃Si