(3aR,4S,7S,7aR)-4-((E)-3-Acetoxy-propenyl)-6-benzenesulfinylmethyl-2-benzoyl-1-benzyl-7-methyl-3-oxo-1,2,3,4,7,7a-hexahydro-isoindole-3a-carboxylic acid ethyl ester

Base Information

Chemical Name:(3aR,4S,7S,7aR)-4-((E)-3-Acetoxy-propenyl)-6-benzenesulfinylmethyl-2-benzoyl-1-benzyl-7-methyl-3-oxo-1,2,3,4,7,7a-hexahydro-isoindole-3a-carboxylic acid ethyl ester
CAS No.:80441-01-6
Molecular Formula:C₃₈H₃₉NO₇S
Molecular Weight:653.796
Hs Code.:

(3aR,4S,7S,7aR)-4-((E)-3-Acetoxy-propenyl)-6-benzenesulfinylmethyl-2-benzoyl-1-benzyl-7-methyl-3-oxo-1,2,3,4,7,7a-hexahydro-isoindole-3a-carboxylic acid ethyl ester

Synonyms:(3aR,4S,7S,7aR)-4-((E)-3-Acetoxy-propenyl)-6-benzenesulfinylmethyl-2-benzoyl-1-benzyl-7-methyl-3-oxo-1,2,3,4,7,7a-hexahydro-isoindole-3a-carboxylic acid ethyl ester

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Chemical Property of (3aR,4S,7S,7aR)-4-((E)-3-Acetoxy-propenyl)-6-benzenesulfinylmethyl-2-benzoyl-1-benzyl-7-methyl-3-oxo-1,2,3,4,7,7a-hexahydro-isoindole-3a-carboxylic acid ethyl ester

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Technology Process of (3aR,4S,7S,7aR)-4-((E)-3-Acetoxy-propenyl)-6-benzenesulfinylmethyl-2-benzoyl-1-benzyl-7-methyl-3-oxo-1,2,3,4,7,7a-hexahydro-isoindole-3a-carboxylic acid ethyl ester

There total 15 articles about (3aR,4S,7S,7aR)-4-((E)-3-Acetoxy-propenyl)-6-benzenesulfinylmethyl-2-benzoyl-1-benzyl-7-methyl-3-oxo-1,2,3,4,7,7a-hexahydro-isoindole-3a-carboxylic acid ethyl 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: 93.0%

: 80361-10-0
(3aR,4S,7S,7aR)-4-((E)-3-Acetoxy-propenyl)-2-benzoyl-1-benzyl-7-methyl-3-oxo-6-phenylsulfanylmethyl-1,2,3,4,7,7a-hexahydro-isoindole-3a-carboxylic acid ethyl ester

: 80441-01-6
(3aR,4S,7S,7aR)-4-((E)-3-Acetoxy-propenyl)-6-benzenesulfinylmethyl-2-benzoyl-1-benzyl-7-methyl-3-oxo-1,2,3,4,7,7a-hexahydro-isoindole-3a-carboxylic acid ethyl ester

Guidance literature:: With sodium periodate; In methanol; water; for 35h; Ambient temperature;
DOI:10.1021/jo00347a034

Reference yield:

: 90741-72-3
rac-1-benzoyl-5-benzylpyrrolidin-2-one

: 80441-01-6
(3aR,4S,7S,7aR)-4-((E)-3-Acetoxy-propenyl)-6-benzenesulfinylmethyl-2-benzoyl-1-benzyl-7-methyl-3-oxo-1,2,3,4,7,7a-hexahydro-isoindole-3a-carboxylic acid ethyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: LDA, hexamethylphosphoramide / 1.) THF, -78 deg C, 45 min, 2.) -78 deg C to RT, 2 h

2: 1.) LDA, HMPA / 1.) THF, -78 deg C, 45 min, 2.) -78 deg C to RT, 2 h

3: 64 percent / 30percent H₂O₂, glacial acetic acid / H₂O; tetrahydrofuran / 2 h / 0 °C

4: 28 percent / hexane / 1 h / 125 °C

5: 93 percent / sodium periodate / methanol; H₂O / 35 h / Ambient temperature

With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium periodate; dihydrogen peroxide; acetic acid; lithium diisopropyl amide; In tetrahydrofuran; methanol; hexane; water;
DOI:10.1021/jo00347a034

Reference yield:

: 80360-83-4
(Z)-2-<(phenylthio)methyl>-2-butenal

: 80441-01-6
(3aR,4S,7S,7aR)-4-((E)-3-Acetoxy-propenyl)-6-benzenesulfinylmethyl-2-benzoyl-1-benzyl-7-methyl-3-oxo-1,2,3,4,7,7a-hexahydro-isoindole-3a-carboxylic acid ethyl ester

Guidance literature:: Multi-step reaction with 6 steps

2: 1.) NaH / 1.) THF, below 30 deg C, 1 h, 2.) 60 deg C, 15 min

3: DIBAL / hexane; CH₂Cl₂ / 0.5 h / 0 °C

4: 89 percent / triethylamine, p-(dimethylamino)pyridine / diethyl ether / 3 h / Ambient temperature

5: 28 percent / hexane / 1 h / 125 °C

6: 93 percent / sodium periodate / methanol; H₂O / 35 h / Ambient temperature

With dmap; sodium periodate; sodium hydride; diisobutylaluminium hydride; triethylamine; In methanol; diethyl ether; hexane; dichloromethane; water;
DOI:10.1021/jo00347a034