(3S,4R)-4-{(1R,3S)-3-[2-(4-Benzenesulfonyl-piperazin-1-yl)-2-oxo-ethoxy]-2-oxo-cyclohexyl}-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-azetidin-2-one

Base Information

• Chemical Name: (3S,4R)-4-{(1R,3S)-3-[2-(4-Benzenesulfonyl-piperazin-1-yl)-2-oxo-ethoxy]-2-oxo-cyclohexyl}-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-azetidin-2-one
• CAS No.: 198402-35-6
• Molecular Formula: C₂₉H₄₅N₃O₇SSi
• Molecular Weight: 607.844

Synonyms:

Chemical Property of (3S,4R)-4-{(1R,3S)-3-[2-(4-Benzenesulfonyl-piperazin-1-yl)-2-oxo-ethoxy]-2-oxo-cyclohexyl}-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-azetidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4R)-4-{(1R,3S)-3-[2-(4-Benzenesulfonyl-piperazin-1-yl)-2-oxo-ethoxy]-2-oxo-cyclohexyl}-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-azetidin-2-one

There total 11 articles about (3S,4R)-4-{(1R,3S)-3-[2-(4-Benzenesulfonyl-piperazin-1-yl)-2-oxo-ethoxy]-2-oxo-cyclohexyl}-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-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:

(3S,4R)-4-[(1R,2S,3R)-2,3-epoxycyclohexyl]-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]azetidin-2-one (135297-04-0) → (3S,4R)-4-{(1R,3S)-3-[2-(4-Benzenesulfonyl-piperazin-1-yl)-2-oxo-ethoxy]-2-oxo-cyclohexyl}-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-azetidin-2-one (198402-35-6)

Guidance literature:

Multi-step reaction with 11 steps

1: 53 percent / ceric ammonium nitrate / acetonitrile / 20 h / Ambient temperature

2: 79 percent / 2,6-lutidine / CH₂Cl₂ / 5 °C

3: 92 percent / H₂ / Pd/C / ethyl acetate / 2 h / 760 Torr

4: 72 percent / 2(OAc)>4 / CH₂Cl₂ / 6 h / Ambient temperature

5: 60 percent / potassium tert-butoxide / 2 h / -20 deg C -> room temperature

6: 55 percent / tetrabutylammonium fluoride, glacial acetic acid / tetrahydrofuran / 2 h / Ambient temperature

7: 1.) 2,6-lutidine, 2.) Pd(PPh₃)4, sodium 2-ethylhexanoate, buffer pH=3 / 1.) CH₂Cl₂

8: PPh₃ / CH₂Cl₂

9: CH₂Cl₂ / 1 h

10: 83 percent / tetrabutylammonium fluoride, glacial acetic acid / tetrahydrofuran / 1 h

11: 50 percent / oxalyl chloride, DMSO, Et₃N / CH₂Cl₂ / 1.) -60 deg C, 30 min, 2.) -20 deg C, 2 h

With 2,6-dimethylpyridine; dirhodium tetraacetate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; oxalyl dichloride; ammonium cerium(IV) nitrate; buffer pH=3; potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; acetic acid; dimethyl sulfoxide; triethylamine; triphenylphosphine; sodium 2-ethylhexanoic acid; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; ethyl acetate; acetonitrile;

DOI:10.1016/S0040-4020(97)01053-3

Reference yield:

(3S,4R)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-((1R,2S,3S)-2-hydroxy-3-nitrooxy-cyclohexyl)-azetidin-2-one (190973-56-9) → (3S,4R)-4-{(1R,3S)-3-[2-(4-Benzenesulfonyl-piperazin-1-yl)-2-oxo-ethoxy]-2-oxo-cyclohexyl}-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-azetidin-2-one (198402-35-6)

Guidance literature:

Multi-step reaction with 10 steps

1: 79 percent / 2,6-lutidine / CH₂Cl₂ / 5 °C

2: 92 percent / H₂ / Pd/C / ethyl acetate / 2 h / 760 Torr

3: 72 percent / 2(OAc)>4 / CH₂Cl₂ / 6 h / Ambient temperature

4: 60 percent / potassium tert-butoxide / 2 h / -20 deg C -> room temperature

5: 55 percent / tetrabutylammonium fluoride, glacial acetic acid / tetrahydrofuran / 2 h / Ambient temperature

6: 1.) 2,6-lutidine, 2.) Pd(PPh₃)4, sodium 2-ethylhexanoate, buffer pH=3 / 1.) CH₂Cl₂

7: PPh₃ / CH₂Cl₂

8: CH₂Cl₂ / 1 h

9: 83 percent / tetrabutylammonium fluoride, glacial acetic acid / tetrahydrofuran / 1 h

10: 50 percent / oxalyl chloride, DMSO, Et₃N / CH₂Cl₂ / 1.) -60 deg C, 30 min, 2.) -20 deg C, 2 h

With 2,6-dimethylpyridine; dirhodium tetraacetate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; oxalyl dichloride; buffer pH=3; potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; acetic acid; dimethyl sulfoxide; triethylamine; triphenylphosphine; sodium 2-ethylhexanoic acid; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; ethyl acetate;

DOI:10.1016/S0040-4020(97)01053-3

Reference yield:

(1S,4aS,5S,8aR,8bR)-3,3-Di-tert-butyl-1-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-5-nitrooxy-octahydro-4-oxa-2a-aza-3-sila-cyclobuta[a]naphthalen-2-one (190973-58-1) → (3S,4R)-4-{(1R,3S)-3-[2-(4-Benzenesulfonyl-piperazin-1-yl)-2-oxo-ethoxy]-2-oxo-cyclohexyl}-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-azetidin-2-one (198402-35-6)

Guidance literature:

Multi-step reaction with 9 steps

1: 92 percent / H₂ / Pd/C / ethyl acetate / 2 h / 760 Torr

2: 72 percent / 2(OAc)>4 / CH₂Cl₂ / 6 h / Ambient temperature

3: 60 percent / potassium tert-butoxide / 2 h / -20 deg C -> room temperature

4: 55 percent / tetrabutylammonium fluoride, glacial acetic acid / tetrahydrofuran / 2 h / Ambient temperature

5: 1.) 2,6-lutidine, 2.) Pd(PPh₃)4, sodium 2-ethylhexanoate, buffer pH=3 / 1.) CH₂Cl₂

6: PPh₃ / CH₂Cl₂

7: CH₂Cl₂ / 1 h

8: 83 percent / tetrabutylammonium fluoride, glacial acetic acid / tetrahydrofuran / 1 h

9: 50 percent / oxalyl chloride, DMSO, Et₃N / CH₂Cl₂ / 1.) -60 deg C, 30 min, 2.) -20 deg C, 2 h

With 2,6-dimethylpyridine; dirhodium tetraacetate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; oxalyl dichloride; buffer pH=3; potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; acetic acid; dimethyl sulfoxide; triethylamine; triphenylphosphine; sodium 2-ethylhexanoic acid; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; ethyl acetate;

DOI:10.1016/S0040-4020(97)01053-3

upstream raw materials:

(3S,4R)-4-[(1R,2S,3R)-2,3-epoxycyclohexyl]-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]azetidin-2-one

(3S,4R)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-((1R,2S,3S)-2-hydroxy-3-nitrooxy-cyclohexyl)-azetidin-2-one

(1S,4aS,5S,8aR,8bR)-3,3-Di-tert-butyl-1-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-5-hydroxy-octahydro-4-oxa-2a-aza-3-sila-cyclobuta[a]naphthalen-2-one

(1S,4aS,5S,8aR,8bR)-3,3-Di-tert-butyl-1-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-5-nitrooxy-octahydro-4-oxa-2a-aza-3-sila-cyclobuta[a]naphthalen-2-one

Downstream raw materials:

(1S,5S,8aS,8bR)-5-[2-(4-Benzenesulfonyl-piperazin-1-yl)-2-oxo-ethoxy]-1-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2-oxo-1,2,5,6,7,8,8a,8b-octahydro-azeto[2,1-a]isoindole-4-carboxylic acid allyl ester

(1S,5S,8aS,8bR)-5-[2-(4-Benzenesulfonyl-piperazin-1-yl)-2-oxo-ethoxy]-1-((R)-1-hydroxy-ethyl)-2-oxo-1,2,5,6,7,8,8a,8b-octahydro-azeto[2,1-a]isoindole-4-carboxylic acid allyl ester

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