(R)-3-[(3R,4R)-1-[tert-Butoxycarbonyl-(triphenyl-λ⁵-phosphanylidene)-methyl]-2-oxo-4-(2-oxo-propionylsulfanyl)-azetidin-3-yl]-2,2-dimethyl-4-oxo-5-phenyl-imidazolidine-1-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: (R)-3-[(3R,4R)-1-[tert-Butoxycarbonyl-(triphenyl-λ⁵-phosphanylidene)-methyl]-2-oxo-4-(2-oxo-propionylsulfanyl)-azetidin-3-yl]-2,2-dimethyl-4-oxo-5-phenyl-imidazolidine-1-carboxylic acid tert-butyl ester
• CAS No.: 73933-05-8
• Molecular Formula: C₄₆H₅₀N₃O₈PS
• Molecular Weight: 835.958

Synonyms:

Chemical Property of (R)-3-[(3R,4R)-1-[tert-Butoxycarbonyl-(triphenyl-λ⁵-phosphanylidene)-methyl]-2-oxo-4-(2-oxo-propionylsulfanyl)-azetidin-3-yl]-2,2-dimethyl-4-oxo-5-phenyl-imidazolidine-1-carboxylic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-3-[(3R,4R)-1-[tert-Butoxycarbonyl-(triphenyl-λ⁵-phosphanylidene)-methyl]-2-oxo-4-(2-oxo-propionylsulfanyl)-azetidin-3-yl]-2,2-dimethyl-4-oxo-5-phenyl-imidazolidine-1-carboxylic acid tert-butyl ester

There total 17 articles about (R)-3-[(3R,4R)-1-[tert-Butoxycarbonyl-(triphenyl-λ⁵-phosphanylidene)-methyl]-2-oxo-4-(2-oxo-propionylsulfanyl)-azetidin-3-yl]-2,2-dimethyl-4-oxo-5-phenyl-imidazolidine-1-carboxylic acid tert-butyl ester 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:

hetacillin (3511-16-8) → (R)-3-[(3R,4R)-1-[tert-Butoxycarbonyl-(triphenyl-λ5-phosphanylidene)-methyl]-2-oxo-4-(2-oxo-propionylsulfanyl)-azetidin-3-yl]-2,2-dimethyl-4-oxo-5-phenyl-imidazolidine-1-carboxylic acid tert-butyl ester (73933-05-8)

Guidance literature:

Multi-step reaction with 15 steps

1: 88 percent / CH₂Cl₂; diethyl ether / 0.5 h / 0 °C

2: 79 percent / 90percent m-chloroperbenzoic acid / CH₂Cl₂ / 1.5 h / Ambient temperature

3: 56 percent / benzene / 90 h / Heating

4: 97 percent / Et₃N / CH₂Cl₂ / 1 h / Ambient temperature

5: 89 percent / i-Pr₂NEt / dioxane / 72 h / 50 °C

6: 1.) PH₃P / 1.) H₂O, CH₂Cl₂, 0 to 5 deg C, 88 h, 2.) pyridine, RT; 4.5 h

7: 85 percent / AcOH / tetrahydrofuran; H₂O / 21 h / Ambient temperature

8: 7.93 g / O₃ / methanol / 2.17 h / -40 °C

9: methanol; tetrahydrofuran; H₂O / Ambient temperature

10: Et₃N / dimethylformamide / 2 h / Ambient temperature

11: 69 percent / 1N HCl / acetonitrile; H₂O / 17 h / Ambient temperature

12: 573 mg / molecular sieves 4A / dimethylformamide; toluene / 3 h / Ambient temperature

13: 495 mg / SOCl₂, polymeric base / dioxane / 3 h / Ambient temperature

14: 78 percent / polymeric base / dioxane / 38 h / 50 °C

15: 1.) O₃/O₂, 2.) Me₂S / 1.) CH₂Cl₂, TFA, -25 deg C, 42 min, 2.) CH₂Cl₂, TFA, -25 deg C, 17 h

With hydrogenchloride; thionyl chloride; dimethylsulfide; 4 A molecular sieve; polymeric base; oxygen; ozone; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; benzene;

DOI:10.1002/hlca.19800630119

Reference yield:

hetacillin methyl ester (4052-65-7) → (R)-3-[(3R,4R)-1-[tert-Butoxycarbonyl-(triphenyl-λ5-phosphanylidene)-methyl]-2-oxo-4-(2-oxo-propionylsulfanyl)-azetidin-3-yl]-2,2-dimethyl-4-oxo-5-phenyl-imidazolidine-1-carboxylic acid tert-butyl ester (73933-05-8)

Guidance literature:

Multi-step reaction with 14 steps

1: 79 percent / 90percent m-chloroperbenzoic acid / CH₂Cl₂ / 1.5 h / Ambient temperature

2: 56 percent / benzene / 90 h / Heating

3: 97 percent / Et₃N / CH₂Cl₂ / 1 h / Ambient temperature

4: 89 percent / i-Pr₂NEt / dioxane / 72 h / 50 °C

5: 1.) PH₃P / 1.) H₂O, CH₂Cl₂, 0 to 5 deg C, 88 h, 2.) pyridine, RT; 4.5 h

6: 85 percent / AcOH / tetrahydrofuran; H₂O / 21 h / Ambient temperature

7: 7.93 g / O₃ / methanol / 2.17 h / -40 °C

8: methanol; tetrahydrofuran; H₂O / Ambient temperature

9: Et₃N / dimethylformamide / 2 h / Ambient temperature

10: 69 percent / 1N HCl / acetonitrile; H₂O / 17 h / Ambient temperature

11: 573 mg / molecular sieves 4A / dimethylformamide; toluene / 3 h / Ambient temperature

12: 495 mg / SOCl₂, polymeric base / dioxane / 3 h / Ambient temperature

13: 78 percent / polymeric base / dioxane / 38 h / 50 °C

14: 1.) O₃/O₂, 2.) Me₂S / 1.) CH₂Cl₂, TFA, -25 deg C, 42 min, 2.) CH₂Cl₂, TFA, -25 deg C, 17 h

With hydrogenchloride; thionyl chloride; dimethylsulfide; 4 A molecular sieve; polymeric base; oxygen; ozone; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; benzene;

DOI:10.1002/hlca.19800630119

Reference yield:

(R)-2-[(2R,3R)-2-(Benzothiazol-2-yldisulfanyl)-3-((R)-2,2-dimethyl-5-oxo-4-phenyl-imidazolidin-1-yl)-4-oxo-azetidin-1-yl]-3-methyl-but-3-enoic acid methyl ester (73932-88-4) → (R)-3-[(3R,4R)-1-[tert-Butoxycarbonyl-(triphenyl-λ5-phosphanylidene)-methyl]-2-oxo-4-(2-oxo-propionylsulfanyl)-azetidin-3-yl]-2,2-dimethyl-4-oxo-5-phenyl-imidazolidine-1-carboxylic acid tert-butyl ester (73933-05-8)

Guidance literature:

Multi-step reaction with 12 steps

1: 97 percent / Et₃N / CH₂Cl₂ / 1 h / Ambient temperature

2: 89 percent / i-Pr₂NEt / dioxane / 72 h / 50 °C

3: 1.) PH₃P / 1.) H₂O, CH₂Cl₂, 0 to 5 deg C, 88 h, 2.) pyridine, RT; 4.5 h

4: 85 percent / AcOH / tetrahydrofuran; H₂O / 21 h / Ambient temperature

5: 7.93 g / O₃ / methanol / 2.17 h / -40 °C

6: methanol; tetrahydrofuran; H₂O / Ambient temperature

7: Et₃N / dimethylformamide / 2 h / Ambient temperature

8: 69 percent / 1N HCl / acetonitrile; H₂O / 17 h / Ambient temperature

9: 573 mg / molecular sieves 4A / dimethylformamide; toluene / 3 h / Ambient temperature

10: 495 mg / SOCl₂, polymeric base / dioxane / 3 h / Ambient temperature

11: 78 percent / polymeric base / dioxane / 38 h / 50 °C

12: 1.) O₃/O₂, 2.) Me₂S / 1.) CH₂Cl₂, TFA, -25 deg C, 42 min, 2.) CH₂Cl₂, TFA, -25 deg C, 17 h

With hydrogenchloride; thionyl chloride; dimethylsulfide; 4 A molecular sieve; polymeric base; oxygen; ozone; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1002/hlca.19800630119

upstream raw materials:

(R)-3-[(2R,3R)-1-[tert-Butoxycarbonyl-(triphenyl-λ⁵-phosphanylidene)-methyl]-2-(2-methyl-acryloylsulfanyl)-4-oxo-azetidin-3-yl]-2,2-dimethyl-4-oxo-5-phenyl-imidazolidine-1-carboxylic acid tert-butyl ester

t-butyl α,α-dihydroxyacetate

hetacillin

hetacillin methyl ester

Downstream raw materials:

t-butyl 7(R)-(2,2-dimethyl-3-t-butoxycarbonyl-4(R)-phenyl-imidazolid-5-on-1-yl)-3-methyl-2-oxo-(6R)-cephem-4-carboxylate

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