Acetic acid (3aS,4R,5R,7R,7aS)-2-benzoyl-1-benzyl-4-(tert-butyl-dimethyl-silanyloxymethyl)-7-methyl-6-methylene-3-oxo-octahydro-isoindol-5-yl ester

Base Information

Chemical Name:Acetic acid (3aS,4R,5R,7R,7aS)-2-benzoyl-1-benzyl-4-(tert-butyl-dimethyl-silanyloxymethyl)-7-methyl-6-methylene-3-oxo-octahydro-isoindol-5-yl ester
CAS No.:80361-18-8
Molecular Formula:C₃₃H₄₃NO₅Si
Molecular Weight:561.794
Hs Code.:

Acetic acid (3aS,4R,5R,7R,7aS)-2-benzoyl-1-benzyl-4-(tert-butyl-dimethyl-silanyloxymethyl)-7-methyl-6-methylene-3-oxo-octahydro-isoindol-5-yl ester

Synonyms:Acetic acid (3aS,4R,5R,7R,7aS)-2-benzoyl-1-benzyl-4-(tert-butyl-dimethyl-silanyloxymethyl)-7-methyl-6-methylene-3-oxo-octahydro-isoindol-5-yl ester

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Chemical Property of Acetic acid (3aS,4R,5R,7R,7aS)-2-benzoyl-1-benzyl-4-(tert-butyl-dimethyl-silanyloxymethyl)-7-methyl-6-methylene-3-oxo-octahydro-isoindol-5-yl ester

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Technology Process of Acetic acid (3aS,4R,5R,7R,7aS)-2-benzoyl-1-benzyl-4-(tert-butyl-dimethyl-silanyloxymethyl)-7-methyl-6-methylene-3-oxo-octahydro-isoindol-5-yl ester

There total 18 articles about Acetic acid (3aS,4R,5R,7R,7aS)-2-benzoyl-1-benzyl-4-(tert-butyl-dimethyl-silanyloxymethyl)-7-methyl-6-methylene-3-oxo-octahydro-isoindol-5-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:

: 80361-17-7
Acetic acid (3aR,4S,5R,6S,7S,7aR)-6-acetoxy-2-benzoyl-3-benzyl-7-(tert-butyl-dimethyl-silanyloxymethyl)-4-methyl-1-oxo-5-trimethylsilanylmethyl-octahydro-isoindol-5-yl ester

: 80361-18-8
Acetic acid (3aS,4R,5R,7R,7aS)-2-benzoyl-1-benzyl-4-(tert-butyl-dimethyl-silanyloxymethyl)-7-methyl-6-methylene-3-oxo-octahydro-isoindol-5-yl ester

Guidance literature:: With dmap; thionyl chloride; In pyridine; at 0 ℃; for 1.5h; Yield given;
DOI:10.1021/jo00347a034

Reference yield:

: 88517-80-0
5-benzyl-2,4-pyrrolidinedione

: 80361-18-8
Acetic acid (3aS,4R,5R,7R,7aS)-2-benzoyl-1-benzyl-4-(tert-butyl-dimethyl-silanyloxymethyl)-7-methyl-6-methylene-3-oxo-octahydro-isoindol-5-yl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 75 percent / sodium cyanoborohydride, chloroacetic acid / methanol / 1 h / Ambient temperature

2: n-BuLi / tetrahydrofuran; hexane / -78 - 25 °C

3: triethylamine / tetrahydrofuran; hexane

4: 62 percent / 2,6-di-tert-butylhydroquinone / toluene / 78 h / 150 °C

5: 80 percent / OsO₄ / pyridine / 1 h / 20 °C

6: pyridine / 14 h / 20 °C

7: thionyl chloride, 4-(dimethylamino)pyridine / pyridine / 1.5 h / 0 °C

With dmap; osmium(VIII) oxide; n-butyllithium; thionyl chloride; 2,6-di-tert-butyl-4-hydroxyphenol; sodium cyanoborohydride; triethylamine; chloroacetic acid; In tetrahydrofuran; pyridine; methanol; hexane; toluene;
DOI:10.1021/jo00347a034

Reference yield:

: 1795-96-6
phenylalanine ethyl ester

: 80361-18-8
Acetic acid (3aS,4R,5R,7R,7aS)-2-benzoyl-1-benzyl-4-(tert-butyl-dimethyl-silanyloxymethyl)-7-methyl-6-methylene-3-oxo-octahydro-isoindol-5-yl ester

Guidance literature:: Multi-step reaction with 10 steps

1: 100 percent / K₂CO₃ / diethyl ether; H₂O / ice bath

2: sodium ethanolate / ethanol; diethyl ether / 15 h / Ambient temperature

3: 90 percent / acetonitrile; H₂O / 2 h / 70 °C

4: 75 percent / sodium cyanoborohydride, chloroacetic acid / methanol / 1 h / Ambient temperature

5: n-BuLi / tetrahydrofuran; hexane / -78 - 25 °C

6: triethylamine / tetrahydrofuran; hexane

7: 62 percent / 2,6-di-tert-butylhydroquinone / toluene / 78 h / 150 °C

8: 80 percent / OsO₄ / pyridine / 1 h / 20 °C

9: pyridine / 14 h / 20 °C

10: thionyl chloride, 4-(dimethylamino)pyridine / pyridine / 1.5 h / 0 °C

With dmap; osmium(VIII) oxide; n-butyllithium; thionyl chloride; 2,6-di-tert-butyl-4-hydroxyphenol; sodium ethanolate; sodium cyanoborohydride; potassium carbonate; triethylamine; chloroacetic acid; In tetrahydrofuran; pyridine; methanol; diethyl ether; ethanol; hexane; water; toluene; acetonitrile;
DOI:10.1021/jo00347a034