1-Azetidinecarboxylic acid, 2-[[[(1,1-dimethylethyl)diphenylsilyl]oxy]methyl]-3-oxo-4-propyl-, 1,1-dimethylethyl ester, (2S,4R)-

Base Information

• Chemical Name: 1-Azetidinecarboxylic acid, 2-[[[(1,1-dimethylethyl)diphenylsilyl]oxy]methyl]-3-oxo-4-propyl-, 1,1-dimethylethyl ester, (2S,4R)-
• CAS No.: 702702-10-1
• Molecular Formula: C28H39NO4Si
• Molecular Weight: 481.707
• Mol file: 702702-10-1.mol

Synonyms:

Chemical Property of 1-Azetidinecarboxylic acid, 2-[[[(1,1-dimethylethyl)diphenylsilyl]oxy]methyl]-3-oxo-4-propyl-, 1,1-dimethylethyl ester, (2S,4R)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-Azetidinecarboxylic acid, 2-[[[(1,1-dimethylethyl)diphenylsilyl]oxy]methyl]-3-oxo-4-propyl-, 1,1-dimethylethyl ester, (2S,4R)-

There total 7 articles about 1-Azetidinecarboxylic acid, 2-[[[(1,1-dimethylethyl)diphenylsilyl]oxy]methyl]-3-oxo-4-propyl-, 1,1-dimethylethyl ester, (2S,4R)- 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: 35.0%

(2S)-2-(N-tert-butyloxycarbonyl)-amino-1-tert-butyldiphenylsilyloxy-4-diazo-heptan-3-one (702702-09-8) → (2S,4R)-N-(tert-butyloxycarbonyl)-2-(tert-butyldiphenylsilyloxymethyl)-4-propyl-azetidin-3-one (702702-10-1)

Guidance literature:

dirhodium tetraacetate; In dichloromethane; at 0 ℃; for 1h;

DOI:10.1016/j.tetlet.2004.03.036

Reference yield:

(S)-N-(tert-butoxycarbonyl)serine (3262-72-4) → (2S,4R)-N-(tert-butyloxycarbonyl)-2-(tert-butyldiphenylsilyloxymethyl)-4-propyl-azetidin-3-one (702702-10-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 100 percent / dimethylformamide / 36 h

2: Et₃N / tetrahydrofuran / -21 - 0 °C

3: 50 percent / diethyl ether; tetrahydrofuran / 2 h / 20 °C

4: 35 percent Chromat_. / Rh₂(OAc)4 / CH₂Cl₂ / 1 h / 0 °C

With triethylamine; dirhodium tetraacetate; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.jorganchem.2005.07.016

Reference yield:

(S)-2-tert-butoxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-propionic acid (145790-51-8) → (2S,4R)-N-(tert-butyloxycarbonyl)-2-(tert-butyldiphenylsilyloxymethyl)-4-propyl-azetidin-3-one (702702-10-1)

Guidance literature:

Multi-step reaction with 3 steps

1: Et₃N / tetrahydrofuran / -21 - 0 °C

2: 50 percent / diethyl ether; tetrahydrofuran / 2 h / 20 °C

3: 35 percent Chromat_. / Rh₂(OAc)4 / CH₂Cl₂ / 1 h / 0 °C

With triethylamine; dirhodium tetraacetate; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1016/j.jorganchem.2005.07.016

upstream raw materials:

(2S)-2-(N-tert-butyloxycarbonyl)-amino-1-tert-butyldiphenylsilyloxy-4-diazo-heptan-3-one

(2S,3S,4R)-N-(tert-butyloxycarbonyl)-2-(tert-butyldiphenylsilyloxymethyl)-4-propyl-azetidin-3-ol

(S)-N-(tert-butoxycarbonyl)serine

(S)-2-tert-butoxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-propionic acid

Downstream raw materials:

(2S,3S,4R)-N-(tert-butyloxycarbonyl)-2-hydroxymethyl-4-propyl-azetidin-3-ol

(2S,3S,4R)-N-(tert-butyloxycarbonyl)-2-(tert-butyldiphenylsilyloxymethyl)-4-propyl-azetidin-3-ol