(1S,5S,8aS,8bR)-5-(Benzyloxycarbonyl-methyl-amino)-1-((R)-1-hydroxy-ethyl)-2-oxo-1,2,5,6,7,8,8a,8b-octahydro-azeto[2,1-a]isoindole-4-carboxylic acid 9H-fluoren-9-yl ester

Base Information

Chemical Name:(1S,5S,8aS,8bR)-5-(Benzyloxycarbonyl-methyl-amino)-1-((R)-1-hydroxy-ethyl)-2-oxo-1,2,5,6,7,8,8a,8b-octahydro-azeto[2,1-a]isoindole-4-carboxylic acid 9H-fluoren-9-yl ester
CAS No.:300568-79-0
Molecular Formula:C₃₅H₃₄N₂O₆
Molecular Weight:578.665
Hs Code.:

(1S,5S,8aS,8bR)-5-(Benzyloxycarbonyl-methyl-amino)-1-((R)-1-hydroxy-ethyl)-2-oxo-1,2,5,6,7,8,8a,8b-octahydro-azeto[2,1-a]isoindole-4-carboxylic acid 9H-fluoren-9-yl ester

Synonyms:(1S,5S,8aS,8bR)-5-(Benzyloxycarbonyl-methyl-amino)-1-((R)-1-hydroxy-ethyl)-2-oxo-1,2,5,6,7,8,8a,8b-octahydro-azeto[2,1-a]isoindole-4-carboxylic acid 9H-fluoren-9-yl ester

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Chemical Property of (1S,5S,8aS,8bR)-5-(Benzyloxycarbonyl-methyl-amino)-1-((R)-1-hydroxy-ethyl)-2-oxo-1,2,5,6,7,8,8a,8b-octahydro-azeto[2,1-a]isoindole-4-carboxylic acid 9H-fluoren-9-yl ester

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Technology Process of (1S,5S,8aS,8bR)-5-(Benzyloxycarbonyl-methyl-amino)-1-((R)-1-hydroxy-ethyl)-2-oxo-1,2,5,6,7,8,8a,8b-octahydro-azeto[2,1-a]isoindole-4-carboxylic acid 9H-fluoren-9-yl ester

There total 10 articles about (1S,5S,8aS,8bR)-5-(Benzyloxycarbonyl-methyl-amino)-1-((R)-1-hydroxy-ethyl)-2-oxo-1,2,5,6,7,8,8a,8b-octahydro-azeto[2,1-a]isoindole-4-carboxylic acid 9H-fluoren-9-yl 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: 61.0%

: 300568-77-8
5-(benzyloxycarbonyl-methyl-amino)-1-[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 9H-fluoren-9-yl ester

: 300568-79-0
(1S,5S,8aS,8bR)-5-(Benzyloxycarbonyl-methyl-amino)-1-((R)-1-hydroxy-ethyl)-2-oxo-1,2,5,6,7,8,8a,8b-octahydro-azeto[2,1-a]isoindole-4-carboxylic acid 9H-fluoren-9-yl ester

Guidance literature:: With tetrabutylammomium bromide; acetic acid; cesium fluoride; In tetrahydrofuran; at 40 ℃; for 4h;
DOI:10.1016/S0040-4020(00)00414-2

Reference yield:

: 1689-64-1
9-Fluorenol

: 300568-79-0
(1S,5S,8aS,8bR)-5-(Benzyloxycarbonyl-methyl-amino)-1-((R)-1-hydroxy-ethyl)-2-oxo-1,2,5,6,7,8,8a,8b-octahydro-azeto[2,1-a]isoindole-4-carboxylic acid 9H-fluoren-9-yl ester

Guidance literature:: Multi-step reaction with 4 steps

1: tetrahydrofuran / 1.5 h / 0 °C

2: 94.6 percent / potassium carbonate; pyridine / CH₂Cl₂ / 0 - 25 °C

3: 88.5 percent / P(OEt)3 / various solvent(s) / 5 h / Heating

4: 61 percent / tetrabutylammonium bromide; aq. AcOH; cesium fluoride / tetrahydrofuran / 4 h / 40 °C

With pyridine; tetrabutylammomium bromide; potassium carbonate; acetic acid; cesium fluoride; triethyl phosphite; In tetrahydrofuran; dichloromethane; 1: Substitution / 2: Acylation / 3: Cyclization / 4: desilylation;
DOI:10.1016/S0040-4020(00)00414-2

Reference yield:

: 501-53-1,94274-21-2
benzyl chloroformate

: 300568-79-0
(1S,5S,8aS,8bR)-5-(Benzyloxycarbonyl-methyl-amino)-1-((R)-1-hydroxy-ethyl)-2-oxo-1,2,5,6,7,8,8a,8b-octahydro-azeto[2,1-a]isoindole-4-carboxylic acid 9H-fluoren-9-yl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 86 percent / diisopropylamine / CH₂Cl₂ / 2 h / 0 °C

2: 79 percent / oxalyl chloride; dimethyl sulfoxide / CH₂Cl₂ / 1 h / -70 °C

3: 94.6 percent / potassium carbonate; pyridine / CH₂Cl₂ / 0 - 25 °C

4: 88.5 percent / P(OEt)3 / various solvent(s) / 5 h / Heating

5: 61 percent / tetrabutylammonium bromide; aq. AcOH; cesium fluoride / tetrahydrofuran / 4 h / 40 °C

With pyridine; oxalyl dichloride; tetrabutylammomium bromide; potassium carbonate; acetic acid; dimethyl sulfoxide; diisopropylamine; cesium fluoride; triethyl phosphite; In tetrahydrofuran; dichloromethane; 1: Acylation / 2: Oxidation / 3: Acylation / 4: Cyclization / 5: desilylation;
DOI:10.1016/S0040-4020(00)00414-2