(1S,4aS,5S,8aR,8bR)-5-[2-(4-Benzenesulfonyl-piperazin-1-yl)-2-oxo-ethoxy]-3,3-di-tert-butyl-1-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-octahydro-4-oxa-2a-aza-3-sila-cyclobuta[a]naphthalen-2-one

Base Information

• Chemical Name: (1S,4aS,5S,8aR,8bR)-5-[2-(4-Benzenesulfonyl-piperazin-1-yl)-2-oxo-ethoxy]-3,3-di-tert-butyl-1-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-octahydro-4-oxa-2a-aza-3-sila-cyclobuta[a]naphthalen-2-one
• CAS No.: 198402-21-0
• Molecular Formula: C₃₇H₆₃N₃O₇SSi₂
• Molecular Weight: 750.16

Synonyms:(1S,4aS,5S,8aR,8bR)-5-[2-(4-Benzenesulfonyl-piperazin-1-yl)-2-oxo-ethoxy]-3,3-di-tert-butyl-1-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-octahydro-4-oxa-2a-aza-3-sila-cyclobuta[a]naphthalen-2-one

Chemical Property of (1S,4aS,5S,8aR,8bR)-5-[2-(4-Benzenesulfonyl-piperazin-1-yl)-2-oxo-ethoxy]-3,3-di-tert-butyl-1-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-octahydro-4-oxa-2a-aza-3-sila-cyclobuta[a]naphthalen-2-one

Chemical Property:

Purity/Quality:

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Useful:

Technology Process of (1S,4aS,5S,8aR,8bR)-5-[2-(4-Benzenesulfonyl-piperazin-1-yl)-2-oxo-ethoxy]-3,3-di-tert-butyl-1-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-octahydro-4-oxa-2a-aza-3-sila-cyclobuta[a]naphthalen-2-one

There total 10 articles about (1S,4aS,5S,8aR,8bR)-5-[2-(4-Benzenesulfonyl-piperazin-1-yl)-2-oxo-ethoxy]-3,3-di-tert-butyl-1-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-octahydro-4-oxa-2a-aza-3-sila-cyclobuta[a]naphthalen-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) → (1S,4aS,5S,8aR,8bR)-5-[2-(4-Benzenesulfonyl-piperazin-1-yl)-2-oxo-ethoxy]-3,3-di-tert-butyl-1-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-octahydro-4-oxa-2a-aza-3-sila-cyclobuta[a]naphthalen-2-one (198402-21-0)

Guidance literature:

Multi-step reaction with 9 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

With 2,6-dimethylpyridine; dirhodium tetraacetate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; ammonium cerium(IV) nitrate; buffer pH=3; potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; acetic acid; 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) → (1S,4aS,5S,8aR,8bR)-5-[2-(4-Benzenesulfonyl-piperazin-1-yl)-2-oxo-ethoxy]-3,3-di-tert-butyl-1-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-octahydro-4-oxa-2a-aza-3-sila-cyclobuta[a]naphthalen-2-one (198402-21-0)

Guidance literature:

Multi-step reaction with 8 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

With 2,6-dimethylpyridine; dirhodium tetraacetate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; buffer pH=3; potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; acetic acid; 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-hydroxy-octahydro-4-oxa-2a-aza-3-sila-cyclobuta[a]naphthalen-2-one (190973-61-6) → (1S,4aS,5S,8aR,8bR)-5-[2-(4-Benzenesulfonyl-piperazin-1-yl)-2-oxo-ethoxy]-3,3-di-tert-butyl-1-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-octahydro-4-oxa-2a-aza-3-sila-cyclobuta[a]naphthalen-2-one (198402-21-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 72 percent / 2(OAc)>4 / CH₂Cl₂ / 6 h / Ambient temperature

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

3: 55 percent / tetrabutylammonium fluoride, glacial acetic acid / tetrahydrofuran / 2 h / Ambient temperature

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

5: PPh₃ / CH₂Cl₂

6: CH₂Cl₂ / 1 h

With 2,6-dimethylpyridine; dirhodium tetraacetate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; buffer pH=3; potassium tert-butylate; tetrabutyl ammonium fluoride; acetic acid; triphenylphosphine; sodium 2-ethylhexanoic acid; In tetrahydrofuran; dichloromethane;

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

upstream raw materials:

di-tert-butylsilyl bis(trifluoromethanesulfonate)

(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

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

(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

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

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