(1S,5S,8aS,8bR)-1-((R)-1-Hydroxy-ethyl)-5-methoxy-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,5S,8aS,8bR)-1-((R)-1-Hydroxy-ethyl)-5-methoxy-2-oxo-1,2,5,6,7,8,8a,8b-octahydro-azeto[2,1-a]isoindole-4-carboxylic acid benzyl ester
CAS No.:135446-51-4
Molecular Formula:C₂₁H₂₅NO₅
Molecular Weight:371.433
Hs Code.:

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

There total 9 articles about (1S,5S,8aS,8bR)-1-((R)-1-Hydroxy-ethyl)-5-methoxy-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: 88.0%

: 181798-23-2
(1S,5S,8aS,8bR)-1-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-5-methoxy-2-oxo-1,2,5,6,7,8,8a,8b-octahydro-azeto[2,1-a]isoindole-4-carboxylic acid benzyl ester

: 135446-51-4
(1S,5S,8aS,8bR)-1-((R)-1-Hydroxy-ethyl)-5-methoxy-2-oxo-1,2,5,6,7,8,8a,8b-octahydro-azeto[2,1-a]isoindole-4-carboxylic acid benzyl ester

Guidance literature:: With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; for 96h; Ambient temperature;
DOI:10.1021/ja962006n

Reference yield:

: 7429-44-9
2-methoxycyclohexanone

: 135446-51-4
(1S,5S,8aS,8bR)-1-((R)-1-Hydroxy-ethyl)-5-methoxy-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 8 steps

1: 1.) NaH, KH / 1.) THF, reflux, 2.) THF, reflux, 12 h

2: 1.) NaH / 1.) THF, -20 deg C, 45 min, 2.) THF, -20 deg C, 2 h

3: 2,6-lutidine / CH₂Cl₂ / 0.5 h

4: 37 percent / palladium acetate, triphenylphosphine, formic acid / ethyl acetate / 2.5 h / Heating

5: 90 percent / tetrabutylammonium fluoride, acetic acid / tetrahydrofuran / 0.5 h

6: 97 percent / pyridine / CH₂Cl₂ / 3 h / Ambient temperature

7: 83 percent / triethyl phosphite / xylene / 14 h / 155 - 160 °C

8: 88 percent / tetrabutylammonium fluoride, acetic acid / tetrahydrofuran / 96 h / Ambient temperature

With pyridine; 2,6-dimethylpyridine; formic acid; tetrabutyl ammonium fluoride; palladium diacetate; potassium hydride; sodium hydride; acetic acid; triphenylphosphine; triethyl phosphite; In tetrahydrofuran; dichloromethane; ethyl acetate; xylene;
DOI:10.1021/ja962006n

Reference yield:

: 35249-73-1
benzyl chlorooxalate

: 135446-51-4
(1S,5S,8aS,8bR)-1-((R)-1-Hydroxy-ethyl)-5-methoxy-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 3 steps

1: 97 percent / pyridine / CH₂Cl₂ / 3 h / Ambient temperature

2: 83 percent / triethyl phosphite / xylene / 14 h / 155 - 160 °C

3: 88 percent / tetrabutylammonium fluoride, acetic acid / tetrahydrofuran / 96 h / Ambient temperature

With pyridine; tetrabutyl ammonium fluoride; acetic acid; triethyl phosphite; In tetrahydrofuran; dichloromethane; xylene;
DOI:10.1021/ja962006n