(3S,4S)-4-Benzyl-1-(tert-butyl-dimethyl-silanyl)-3-methyl-azetidin-2-one

Base Information

• Chemical Name: (3S,4S)-4-Benzyl-1-(tert-butyl-dimethyl-silanyl)-3-methyl-azetidin-2-one
• CAS No.: 211618-79-0
• Molecular Formula: C₁₇H₂₇NOSi
• Molecular Weight: 289.493
• Mol file: 211618-79-0.mol

Synonyms:(3S,4S)-4-Benzyl-1-(tert-butyl-dimethyl-silanyl)-3-methyl-azetidin-2-one

Chemical Property of (3S,4S)-4-Benzyl-1-(tert-butyl-dimethyl-silanyl)-3-methyl-azetidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4S)-4-Benzyl-1-(tert-butyl-dimethyl-silanyl)-3-methyl-azetidin-2-one

There total 7 articles about (3S,4S)-4-Benzyl-1-(tert-butyl-dimethyl-silanyl)-3-methyl-azetidin-2-one 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:

N-Cbz-L-Phe (1161-13-3) → (3S,4S)-4-Benzyl-1-(tert-butyl-dimethyl-silanyl)-3-methyl-azetidin-2-one (211618-79-0)

Guidance literature:

Multi-step reaction with 7 steps

1: Et₃N / 13 °C / 1.) -10 deg C, 20 min, 2.) RT, 30 min

2: diethyl ether / 0.17 h / Ambient temperature

3: 63 percent / silver benzoate, Et₃N / 0.5 h / Ambient temperature

4: 93 percent / H₂ / 20percent Pd(OH)2/C / methanol / 7 h / 760 Torr / Ambient temperature

5: 54 percent / NaHCO₃, MsCl / acetonitrile / 16 h / Heating

6: 95 percent / DIEA / CH₂Cl₂ / 16 h / Ambient temperature

7: 1.) LDA / 1.) THF, hexane, -78 deg C, 15 min, 2.) THF, hexane, -78 deg C, 10 min

With hydrogen; silver benzoate; sodium hydrogencarbonate; methanesulfonyl chloride; triethylamine; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; palladium dihydroxide; In methanol; diethyl ether; dichloromethane; acetonitrile;

DOI:10.1021/jm980131z

Reference yield:

(S)-3-[(benzyloxycarbonyl)amino]-1-diazo-4-phenyl-2-butanone (15196-02-8) → (3S,4S)-4-Benzyl-1-(tert-butyl-dimethyl-silanyl)-3-methyl-azetidin-2-one (211618-79-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 63 percent / silver benzoate, Et₃N / 0.5 h / Ambient temperature

2: 93 percent / H₂ / 20percent Pd(OH)2/C / methanol / 7 h / 760 Torr / Ambient temperature

3: 54 percent / NaHCO₃, MsCl / acetonitrile / 16 h / Heating

4: 95 percent / DIEA / CH₂Cl₂ / 16 h / Ambient temperature

5: 1.) LDA / 1.) THF, hexane, -78 deg C, 15 min, 2.) THF, hexane, -78 deg C, 10 min

With hydrogen; silver benzoate; sodium hydrogencarbonate; methanesulfonyl chloride; triethylamine; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; palladium dihydroxide; In methanol; dichloromethane; acetonitrile;

DOI:10.1021/jm980131z

Reference yield:

Z-Phe-O-COO-isoBu (41518-17-6) → (3S,4S)-4-Benzyl-1-(tert-butyl-dimethyl-silanyl)-3-methyl-azetidin-2-one (211618-79-0)

Guidance literature:

Multi-step reaction with 6 steps

1: diethyl ether / 0.17 h / Ambient temperature

2: 63 percent / silver benzoate, Et₃N / 0.5 h / Ambient temperature

3: 93 percent / H₂ / 20percent Pd(OH)2/C / methanol / 7 h / 760 Torr / Ambient temperature

4: 54 percent / NaHCO₃, MsCl / acetonitrile / 16 h / Heating

5: 95 percent / DIEA / CH₂Cl₂ / 16 h / Ambient temperature

6: 1.) LDA / 1.) THF, hexane, -78 deg C, 15 min, 2.) THF, hexane, -78 deg C, 10 min

With hydrogen; silver benzoate; sodium hydrogencarbonate; methanesulfonyl chloride; triethylamine; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; palladium dihydroxide; In methanol; diethyl ether; dichloromethane; acetonitrile;

DOI:10.1021/jm980131z

upstream raw materials:

(S)-4-Benzyl-1-(tert-butyl-dimethyl-silanyl)-azetidin-2-one

methyl iodide

N-Cbz-L-Phe

(S)-3-[(benzyloxycarbonyl)amino]-1-diazo-4-phenyl-2-butanone

Downstream raw materials:

(3R,4S)-4-Benzyl-1-(tert-butyl-dimethyl-silanyl)-3-methyl-azetidin-2-one

4(S)-benzyl-3(S)-methylazetidin-2-one