(3R,4R)-4-acetoxy-3-<(1S)-1-t-butyldimethylsilyloxymethyl-1-((1S)-1-phenylethylaminocarbonyl)>azetidin-2-one

Base Information

• Chemical Name: (3R,4R)-4-acetoxy-3-<(1S)-1-t-butyldimethylsilyloxymethyl-1-((1S)-1-phenylethylaminocarbonyl)>azetidin-2-one
• CAS No.: 114376-78-2
• Molecular Formula: C₂₁H₃₂N₂O₅Si
• Molecular Weight: 420.581

Synonyms:(3R,4R)-4-acetoxy-3-<(1S)-1-t-butyldimethylsilyloxymethyl-1-((1S)-1-phenylethylaminocarbonyl)>azetidin-2-one

Chemical Property of (3R,4R)-4-acetoxy-3-<(1S)-1-t-butyldimethylsilyloxymethyl-1-((1S)-1-phenylethylaminocarbonyl)>azetidin-2-one

Chemical Property:

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Technology Process of (3R,4R)-4-acetoxy-3-<(1S)-1-t-butyldimethylsilyloxymethyl-1-((1S)-1-phenylethylaminocarbonyl)>azetidin-2-one

There total 8 articles about (3R,4R)-4-acetoxy-3-<(1S)-1-t-butyldimethylsilyloxymethyl-1-((1S)-1-phenylethylaminocarbonyl)>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: 73.0%

(3R,4R)-4-acetoxy-3-<(1S)-1-t-butyldimethylsilyloxymethyl-1-((1S)-1-phenylethylaminocarbonyl)>-1-(4-methoxyphenyl)azetidin-2-one (114315-97-8,114376-77-1) → (3R,4R)-4-acetoxy-3-<(1S)-1-t-butyldimethylsilyloxymethyl-1-((1S)-1-phenylethylaminocarbonyl)>azetidin-2-one (114376-78-2)

Guidance literature:

With ammonium cerium(IV) nitrate; In water; acetonitrile; at 0 ℃; for 0.5h;

DOI:10.1002/jhet.5570250225

Reference yield:

(S)-1-phenyl-ethylamine (2627-86-3) → (3R,4R)-4-acetoxy-3-<(1S)-1-t-butyldimethylsilyloxymethyl-1-((1S)-1-phenylethylaminocarbonyl)>azetidin-2-one (114376-78-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 22 percent / dicyclohexylcarbodiimide, 1-hydroxy-1H-benzotriazole / tetrahydrofuran / 1 h / Ambient temperature

2: 36 percent / 1N tetrabutylammonium fluoride, molecular sieves (4 Angstroems) / tetrahydrofuran / 1.5 h / 0 °C

3: 90 percent / CF₃COOH / CH₂Cl₂ / 3 h / Ambient temperature

4: 31 percent / CH₃COOH, lead tetraaceate / dimethylformamide / 0.08 h / 60 °C

5: 76 percent / 4-methylaminopyridine / dimethylformamide / 216 h / Ambient temperature

6: 73 percent / ceric(IV)ammonium nitrate / H₂O; acetonitrile / 0.5 h / 0 °C

With lead(IV) acetate; 4-(Methylamino)pyridine; ammonium cerium(IV) nitrate; 4 A molecular sieve; tetrabutyl ammonium fluoride; benzotriazol-1-ol; acetic acid; dicyclohexyl-carbodiimide; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1002/jhet.5570250225

Reference yield:

(2RS,3SR)-N-(t-butoxycarbonylmethyl)-N-(4-methoxyphenyl)-3-carboxy-2,3-epoxypropionamide (114315-93-4) → (3R,4R)-4-acetoxy-3-<(1S)-1-t-butyldimethylsilyloxymethyl-1-((1S)-1-phenylethylaminocarbonyl)>azetidin-2-one (114376-78-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 22 percent / dicyclohexylcarbodiimide, 1-hydroxy-1H-benzotriazole / tetrahydrofuran / 1 h / Ambient temperature

2: 36 percent / 1N tetrabutylammonium fluoride, molecular sieves (4 Angstroems) / tetrahydrofuran / 1.5 h / 0 °C

3: 90 percent / CF₃COOH / CH₂Cl₂ / 3 h / Ambient temperature

4: 31 percent / CH₃COOH, lead tetraaceate / dimethylformamide / 0.08 h / 60 °C

5: 76 percent / 4-methylaminopyridine / dimethylformamide / 216 h / Ambient temperature

6: 73 percent / ceric(IV)ammonium nitrate / H₂O; acetonitrile / 0.5 h / 0 °C

With lead(IV) acetate; 4-(Methylamino)pyridine; ammonium cerium(IV) nitrate; 4 A molecular sieve; tetrabutyl ammonium fluoride; benzotriazol-1-ol; acetic acid; dicyclohexyl-carbodiimide; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1002/jhet.5570250225

upstream raw materials:

(3R,4R)-4-acetoxy-3-<(1S)-1-t-butyldimethylsilyloxymethyl-1-((1S)-1-phenylethylaminocarbonyl)>-1-(4-methoxyphenyl)azetidin-2-one

(S)-1-phenyl-ethylamine

(2RS,3SR)-N-(t-butoxycarbonylmethyl)-N-(4-methoxyphenyl)-3-carboxy-2,3-epoxypropionamide

(2RS,3SR)-N-(t-butoxycarbonylmethyl)-N-(4-methoxyphenyl)-3-methoxycarbonyl-2,3-epoxypropionate

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