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

Base Information

Chemical Name:(1S,6S,8aS,8bR)-1-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-6-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2-oxo-1,2,5,6,7,8,8a,8b-octahydro-azeto[2,1-a]isoindole-4-carboxylic acid benzyl ester
CAS No.:194535-56-3
Molecular Formula:C₃₄H₅₅NO₅Si₂
Molecular Weight:613.985
Hs Code.:

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

Synonyms:(1S,6S,8aS,8bR)-1-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-6-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2-oxo-1,2,5,6,7,8,8a,8b-octahydro-azeto[2,1-a]isoindole-4-carboxylic acid benzyl ester

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Chemical Property of (1S,6S,8aS,8bR)-1-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-6-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2-oxo-1,2,5,6,7,8,8a,8b-octahydro-azeto[2,1-a]isoindole-4-carboxylic acid benzyl ester

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Technology Process of (1S,6S,8aS,8bR)-1-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-6-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2-oxo-1,2,5,6,7,8,8a,8b-octahydro-azeto[2,1-a]isoindole-4-carboxylic acid benzyl ester

There total 12 articles about (1S,6S,8aS,8bR)-1-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-6-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2-oxo-1,2,5,6,7,8,8a,8b-octahydro-azeto[2,1-a]isoindole-4-carboxylic acid benzyl 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: 56.0%

: 194535-54-1
((2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-{(1R,4R)-4-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2-oxo-cyclohexyl}-4-oxo-azetidin-1-yl)-oxo-acetic acid benzyl ester

: 194535-56-3
(1S,6S,8aS,8bR)-1-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-6-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2-oxo-1,2,5,6,7,8,8a,8b-octahydro-azeto[2,1-a]isoindole-4-carboxylic acid benzyl ester

Guidance literature:: With triethyl phosphite; In o-xylene; at 140 ℃; for 7h;
DOI:10.1016/S0960-894X(97)00326-0

Reference yield:

: 930-68-7
cyclohexenone

: 194535-56-3
(1S,6S,8aS,8bR)-1-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-6-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2-oxo-1,2,5,6,7,8,8a,8b-octahydro-azeto[2,1-a]isoindole-4-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 11 steps

1: 1.) LDA / 1.) THF, -78 deg C, 30 min, 2.) -78 deg C to room temperature, 2 h

2: 1.) NaH / 1.) THF, -20 deg C, 30 min, 2.) -20 deg C, 2 h

3: CH₂Cl₂ / 0.5 h / 0 °C

4: Pd(OAc)2, PPh₃, formic acid / ethyl acetate / 2 h / Heating

5: 1.) n-BuLi / 1.) THF, -78 deg C, 30 min, 2.) -78 deg C, 1 h

6: 1.) O₃, 2.) Me₂S / 1.) CH₂Cl₂, -78 deg C, 2.) -78 deg C to room temperature, 1 h

7: 95 percent / 9-BBN / tetrahydrofuran / 12 h

8: 94 percent / imidazole / dimethylformamide / 12 h / Ambient temperature

9: 78 percent / TBAF, AcOH / tetrahydrofuran / 0.5 h / Ambient temperature

10: 60 percent / pyridine / CH₂Cl₂ / 2 h / 0 °C

11: 56 percent / P(OEt)3 / o-xylene / 7 h / 140 °C

With pyridine; 1H-imidazole; palladium diacetate; 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; formic acid; dimethylsulfide; tetrabutyl ammonium fluoride; sodium hydride; ozone; acetic acid; triphenylphosphine; lithium diisopropyl amide; triethyl phosphite; In tetrahydrofuran; dichloromethane; o-xylene; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1016/S0960-894X(97)00326-0

Reference yield:

: 76899-07-5,78963-47-0,78963-48-1,78963-60-7,80951-41-3,81275-02-7,85647-75-2,85954-95-6,92217-74-8,104527-11-9,76855-69-1
(3R,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-acetoxyazetidin-2-one

: 194535-56-3
(1S,6S,8aS,8bR)-1-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-6-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2-oxo-1,2,5,6,7,8,8a,8b-octahydro-azeto[2,1-a]isoindole-4-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 10 steps

1: 1.) NaH / 1.) THF, -20 deg C, 30 min, 2.) -20 deg C, 2 h

2: CH₂Cl₂ / 0.5 h / 0 °C

3: Pd(OAc)2, PPh₃, formic acid / ethyl acetate / 2 h / Heating

4: 1.) n-BuLi / 1.) THF, -78 deg C, 30 min, 2.) -78 deg C, 1 h

5: 1.) O₃, 2.) Me₂S / 1.) CH₂Cl₂, -78 deg C, 2.) -78 deg C to room temperature, 1 h

6: 95 percent / 9-BBN / tetrahydrofuran / 12 h

7: 94 percent / imidazole / dimethylformamide / 12 h / Ambient temperature

8: 78 percent / TBAF, AcOH / tetrahydrofuran / 0.5 h / Ambient temperature

9: 60 percent / pyridine / CH₂Cl₂ / 2 h / 0 °C

10: 56 percent / P(OEt)3 / o-xylene / 7 h / 140 °C

With pyridine; 1H-imidazole; palladium diacetate; 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; formic acid; dimethylsulfide; tetrabutyl ammonium fluoride; sodium hydride; ozone; acetic acid; triphenylphosphine; triethyl phosphite; In tetrahydrofuran; dichloromethane; o-xylene; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1016/S0960-894X(97)00326-0