(3R,4S)-1-benzoyl-3-triisopropylsilyloxy-4-(m-allyloxyphenyl)azetidin-2-one

Base Information

• Chemical Name: (3R,4S)-1-benzoyl-3-triisopropylsilyloxy-4-(m-allyloxyphenyl)azetidin-2-one
• CAS No.: 360075-38-3
• Molecular Formula: C₂₈H₃₇NO₄Si
• Molecular Weight: 479.692
• Mol file: 360075-38-3.mol

Synonyms:(3R,4S)-1-benzoyl-3-triisopropylsilyloxy-4-(m-allyloxyphenyl)azetidin-2-one

Chemical Property of (3R,4S)-1-benzoyl-3-triisopropylsilyloxy-4-(m-allyloxyphenyl)azetidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4S)-1-benzoyl-3-triisopropylsilyloxy-4-(m-allyloxyphenyl)azetidin-2-one

There total 10 articles about (3R,4S)-1-benzoyl-3-triisopropylsilyloxy-4-(m-allyloxyphenyl)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: 90.0%

benzoyl chloride (98-88-4) + (3R,4S)-3-triisopropylsilyloxy-4-(m-allyloxyphenyl)azetidin-2-one (360075-37-2) → (3R,4S)-1-benzoyl-3-triisopropylsilyloxy-4-(m-allyloxyphenyl)azetidin-2-one (360075-38-3)

Guidance literature:

With dmap; triethylamine; In dichloromethane;

DOI:10.1021/ol016124d

Reference yield:

(3R,4S)-1-(p-methoxyphenyl)-3-hydroxy-4-(m-allyloxyphenyl)azetidin-2-one (941672-58-8) → (3R,4S)-1-benzoyl-3-triisopropylsilyloxy-4-(m-allyloxyphenyl)azetidin-2-one (360075-38-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.15 g / imidazole / dimethylformamide / 8 h / 20 °C

2: 78 percent / aq. ceric ammonium nitrate / acetonitrile / 1.08 h / 0 °C

3: 82 percent / dimethylaminopyridine / CH₂Cl₂ / 1 h / 0 °C

With 1H-imidazole; dmap; ammonium cerium(IV) nitrate; In dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jm061071x

Reference yield:

(rac)-(3RS,4SR)-1-(p-methoxyphenyl)-3-acetyloxy-4-(m-allyloxyphenyl)azetidin-2-one → (3R,4S)-1-benzoyl-3-triisopropylsilyloxy-4-(m-allyloxyphenyl)azetidin-2-one (360075-38-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 48 percent / lipase PS / aq. phosphate buffer; acetonitrile / 74 h / 20 °C / pH 7

2: 99 percent / aq. KOH / tetrahydrofuran / 0.25 h

3: 1.15 g / imidazole / dimethylformamide / 8 h / 20 °C

4: 78 percent / aq. ceric ammonium nitrate / acetonitrile / 1.08 h / 0 °C

5: 82 percent / dimethylaminopyridine / CH₂Cl₂ / 1 h / 0 °C

With 1H-imidazole; dmap; potassium hydroxide; ammonium cerium(IV) nitrate; Lipase PS; In tetrahydrofuran; phosphate buffer; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jm061071x

upstream raw materials:

benzoyl chloride

(3R,4S)-3-triisopropylsilyloxy-4-(m-allyloxyphenyl)azetidin-2-one

triisopropylsilyl chloride

3-allyloxy-benzaldehyde

Downstream raw materials:

C₄₉H₅₁NO₁₅

C₆₄H₈₅NO₁₅Si₂

C₅₁H₅₅NO₁₅

C₆₆H₈₉NO₁₅Si₂