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

Base Information

Chemical Name:(1S,5S,8aS,8bR)-5-Methylamino-2-oxo-1-((R)-1-trimethylsilanyloxy-ethyl)-1,2,5,6,7,8,8a,8b-octahydro-azeto[2,1-a]isoindole-4-carboxylic acid benzyl ester
CAS No.:246546-95-2
Molecular Formula:C₂₄H₃₄N₂O₄Si
Molecular Weight:442.63
Hs Code.:

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

There total 5 articles about (1S,5S,8aS,8bR)-5-Methylamino-2-oxo-1-((R)-1-trimethylsilanyloxy-ethyl)-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:

: 35249-73-1
benzyl chlorooxalate

: 246546-95-2
(1S,5S,8aS,8bR)-5-Methylamino-2-oxo-1-((R)-1-trimethylsilanyloxy-ethyl)-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 4 steps

1: pyridine / CH₂Cl₂ / 0.5 h / 0 °C

2: P(OEt)3 / toluene / 6 h / 110 °C

3: 70 percent / AcOH; TBAF*3H₂O / tetrahydrofuran / 8 h

4: Pd(PPh₃)4 / CH₂Cl₂ / 1 h

With pyridine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetrabutyl ammonium fluoride; acetic acid; triethyl phosphite; In tetrahydrofuran; dichloromethane; toluene; 1: Acylation / 2: Cyclization / 3: desilylation / 4: silylation;
DOI:10.1007/BF02256813

Reference yield:

: 135297-32-4
((1S,3R)-3-{(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-2-oxo-cyclohexyl)-methyl-carbamic acid allyl ester

: 246546-95-2
(1S,5S,8aS,8bR)-5-Methylamino-2-oxo-1-((R)-1-trimethylsilanyloxy-ethyl)-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 4 steps

1: pyridine / CH₂Cl₂ / 0.5 h / 0 °C

2: P(OEt)3 / toluene / 6 h / 110 °C

3: 70 percent / AcOH; TBAF*3H₂O / tetrahydrofuran / 8 h

4: Pd(PPh₃)4 / CH₂Cl₂ / 1 h

With pyridine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetrabutyl ammonium fluoride; acetic acid; triethyl phosphite; In tetrahydrofuran; dichloromethane; toluene; 1: Acylation / 2: Cyclization / 3: desilylation / 4: silylation;
DOI:10.1007/BF02256813

Reference yield:

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

: 246546-95-2
(1S,5S,8aS,8bR)-5-Methylamino-2-oxo-1-((R)-1-trimethylsilanyloxy-ethyl)-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 3 steps

1: P(OEt)3 / toluene / 6 h / 110 °C

2: 70 percent / AcOH; TBAF*3H₂O / tetrahydrofuran / 8 h

3: Pd(PPh₃)4 / CH₂Cl₂ / 1 h

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetrabutyl ammonium fluoride; acetic acid; triethyl phosphite; In tetrahydrofuran; dichloromethane; toluene; 1: Cyclization / 2: desilylation / 3: silylation;
DOI:10.1007/BF02256813