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

Base Information

Chemical Name:(1S,5S,8aS,8bR)-5-Dimethylcarbamoylmethoxy-1-((R)-1-hydroxy-ethyl)-2-oxo-1,2,5,6,7,8,8a,8b-octahydro-azeto[2,1-a]isoindole-4-carboxylic acid 4-tert-butyl-benzyl ester
CAS No.:198402-12-9
Molecular Formula:C₂₈H₃₈N₂O₆
Molecular Weight:498.62
Hs Code.:

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

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

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

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

There total 13 articles about (1S,5S,8aS,8bR)-5-Dimethylcarbamoylmethoxy-1-((R)-1-hydroxy-ethyl)-2-oxo-1,2,5,6,7,8,8a,8b-octahydro-azeto[2,1-a]isoindole-4-carboxylic acid 4-tert-butyl-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: 44.0%

: 198402-11-8
(1S,5S,8aS,8bR)-1-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-5-dimethylcarbamoylmethoxy-2-oxo-1,2,5,6,7,8,8a,8b-octahydro-azeto[2,1-a]isoindole-4-carboxylic acid 4-tert-butyl-benzyl ester

: 198402-12-9
(1S,5S,8aS,8bR)-5-Dimethylcarbamoylmethoxy-1-((R)-1-hydroxy-ethyl)-2-oxo-1,2,5,6,7,8,8a,8b-octahydro-azeto[2,1-a]isoindole-4-carboxylic acid 4-tert-butyl-benzyl ester

Guidance literature:: With tetrabutylammomium bromide; acetic acid; cesium fluoride; In tetrahydrofuran; at 40 ℃; for 24h;
DOI:10.1016/S0040-4020(97)01053-3

Reference yield:

: 135297-04-0
(3S,4R)-4-[(1R,2S,3R)-2,3-epoxycyclohexyl]-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]azetidin-2-one

: 198402-12-9
(1S,5S,8aS,8bR)-5-Dimethylcarbamoylmethoxy-1-((R)-1-hydroxy-ethyl)-2-oxo-1,2,5,6,7,8,8a,8b-octahydro-azeto[2,1-a]isoindole-4-carboxylic acid 4-tert-butyl-benzyl ester

Guidance literature:: Multi-step reaction with 12 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: 90 percent / oxalyl chloride, DMSO / CH₂Cl₂ / 1.) -60 deg C, 30 min, 2.) -20 deg C, 2 h

8: 1.) Et₃N, 2.) P(OEt)3, hydroquinone / 1.) xylene, 0 deg C, 30 min, 2.) xylene, 120 deg C, 4 h

9: Pd(PPh₃)4, PPh₃, sodium 2-ethylhexanoate / tetrahydrofuran / 2 h

10: PPh₃ / acetonitrile / 2 h / Ambient temperature

11: 78 percent / acetonitrile / 0.17 h / Ambient temperature

12: 44 percent / tetrabutylammonium bromide, cesium fluoride, glacial acetic acid / tetrahydrofuran / 24 h / 40 °C

With 2,6-dimethylpyridine; dirhodium tetraacetate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; oxalyl dichloride; ammonium cerium(IV) nitrate; potassium tert-butylate; tetrabutyl ammonium fluoride; tetrabutylammomium bromide; hydrogen; acetic acid; dimethyl sulfoxide; triethylamine; hydroquinone; triphenylphosphine; cesium fluoride; triethyl phosphite; sodium 2-ethylhexanoic acid; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; ethyl acetate; acetonitrile;
DOI:10.1016/S0040-4020(97)01053-3

Reference yield:

: 190973-58-1
(1S,4aS,5S,8aR,8bR)-3,3-Di-tert-butyl-1-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-5-nitrooxy-octahydro-4-oxa-2a-aza-3-sila-cyclobuta[a]naphthalen-2-one

: 198402-12-9
(1S,5S,8aS,8bR)-5-Dimethylcarbamoylmethoxy-1-((R)-1-hydroxy-ethyl)-2-oxo-1,2,5,6,7,8,8a,8b-octahydro-azeto[2,1-a]isoindole-4-carboxylic acid 4-tert-butyl-benzyl ester

Guidance literature:: Multi-step reaction with 10 steps

1: 92 percent / H₂ / Pd/C / ethyl acetate / 2 h / 760 Torr

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

3: 60 percent / potassium tert-butoxide / 2 h / -20 deg C -> room temperature

4: 55 percent / tetrabutylammonium fluoride, glacial acetic acid / tetrahydrofuran / 2 h / Ambient temperature

5: 90 percent / oxalyl chloride, DMSO / CH₂Cl₂ / 1.) -60 deg C, 30 min, 2.) -20 deg C, 2 h

6: 1.) Et₃N, 2.) P(OEt)3, hydroquinone / 1.) xylene, 0 deg C, 30 min, 2.) xylene, 120 deg C, 4 h

7: Pd(PPh₃)4, PPh₃, sodium 2-ethylhexanoate / tetrahydrofuran / 2 h

8: PPh₃ / acetonitrile / 2 h / Ambient temperature

9: 78 percent / acetonitrile / 0.17 h / Ambient temperature

10: 44 percent / tetrabutylammonium bromide, cesium fluoride, glacial acetic acid / tetrahydrofuran / 24 h / 40 °C

With dirhodium tetraacetate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; oxalyl dichloride; potassium tert-butylate; tetrabutyl ammonium fluoride; tetrabutylammomium bromide; hydrogen; acetic acid; dimethyl sulfoxide; triethylamine; hydroquinone; triphenylphosphine; cesium fluoride; triethyl phosphite; sodium 2-ethylhexanoic acid; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; ethyl acetate; acetonitrile;
DOI:10.1016/S0040-4020(97)01053-3