4-Bromo-benzoic acid (3aS,5aS,6S,7R,8S,8aR,8bR)-6-hydroxy-4,7-dimethyl-1-oxo-3,3a,5a,6,7,8,8a,8b-octahydro-1H-indeno[4,5-c]furan-8-yl ester

Base Information

Chemical Name:4-Bromo-benzoic acid (3aS,5aS,6S,7R,8S,8aR,8bR)-6-hydroxy-4,7-dimethyl-1-oxo-3,3a,5a,6,7,8,8a,8b-octahydro-1H-indeno[4,5-c]furan-8-yl ester
CAS No.:443791-97-7
Molecular Formula:C₂₀H₂₁BrO₅
Molecular Weight:421.288
Hs Code.:

Synonyms:4-Bromo-benzoic acid (3aS,5aS,6S,7R,8S,8aR,8bR)-6-hydroxy-4,7-dimethyl-1-oxo-3,3a,5a,6,7,8,8a,8b-octahydro-1H-indeno[4,5-c]furan-8-yl ester

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Chemical Property of 4-Bromo-benzoic acid (3aS,5aS,6S,7R,8S,8aR,8bR)-6-hydroxy-4,7-dimethyl-1-oxo-3,3a,5a,6,7,8,8a,8b-octahydro-1H-indeno[4,5-c]furan-8-yl ester

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Technology Process of 4-Bromo-benzoic acid (3aS,5aS,6S,7R,8S,8aR,8bR)-6-hydroxy-4,7-dimethyl-1-oxo-3,3a,5a,6,7,8,8a,8b-octahydro-1H-indeno[4,5-c]furan-8-yl ester

There total 10 articles about 4-Bromo-benzoic acid (3aS,5aS,6S,7R,8S,8aR,8bR)-6-hydroxy-4,7-dimethyl-1-oxo-3,3a,5a,6,7,8,8a,8b-octahydro-1H-indeno[4,5-c]furan-8-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: 100.0%

: 443791-96-6
(1S,2S,3S,3aR,4R,5S,7aS)-3-(4-Bromo-benzoyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-2,6-dimethyl-1-triisopropylsilanyloxy-2,3,3a,4,5,7a-hexahydro-1H-indene-4-carboxylic acid methyl ester

: 443791-97-7
4-Bromo-benzoic acid (3aS,5aS,6S,7R,8S,8aR,8bR)-6-hydroxy-4,7-dimethyl-1-oxo-3,3a,5a,6,7,8,8a,8b-octahydro-1H-indeno[4,5-c]furan-8-yl ester

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃;
DOI:10.1016/S0040-4039(02)00536-1

Reference yield:

: 156336-31-1
4-methyl-6-<(tert-butyldimethylsilyl)oxy>-2,4-hexadienal

: 443791-97-7
4-Bromo-benzoic acid (3aS,5aS,6S,7R,8S,8aR,8bR)-6-hydroxy-4,7-dimethyl-1-oxo-3,3a,5a,6,7,8,8a,8b-octahydro-1H-indeno[4,5-c]furan-8-yl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 96 percent / n-Bu₂BOTf; Et₃N / CH₂Cl₂ / -78 - 20 °C

2: Me₃Al / tetrahydrofuran / 0 - 20 °C

3: Et₃N / CH₂Cl₂ / 0 °C

4: 94 percent / DIBAL-H / tetrahydrofuran / -78 °C

5: NaHCO₃ / NiCl₂; CrCl₂ / tetrahydrofuran / 20 °C

6: BHT / toluene / 24 h / 80 °C

7: 94 percent / DMAP / CH₂Cl₂ / 20 °C

8: 100 percent / TBAF / tetrahydrofuran / 20 °C

With dmap; 2,6-di-tert-butyl-4-methyl-phenol; di-n-butylboryl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; trimethylaluminum; diisobutylaluminium hydride; sodium hydrogencarbonate; triethylamine; chromium dichloride; nickel dichloride; In tetrahydrofuran; dichloromethane; toluene; 1: Evans reaction / 5: Kishi-Nozaki reaction / 6: intramolecular Diels-Alder reaction;
DOI:10.1016/S0040-4039(02)00536-1

Reference yield:

: (4E,6E)-(2R,3S)-8-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-2,6-dimethyl-octa-4,6-dienoic acid methoxy-methyl-amide

: 443791-97-7
4-Bromo-benzoic acid (3aS,5aS,6S,7R,8S,8aR,8bR)-6-hydroxy-4,7-dimethyl-1-oxo-3,3a,5a,6,7,8,8a,8b-octahydro-1H-indeno[4,5-c]furan-8-yl ester

Guidance literature:: Multi-step reaction with 6 steps

1: Et₃N / CH₂Cl₂ / 0 °C

2: 94 percent / DIBAL-H / tetrahydrofuran / -78 °C

3: NaHCO₃ / NiCl₂; CrCl₂ / tetrahydrofuran / 20 °C

4: BHT / toluene / 24 h / 80 °C

5: 94 percent / DMAP / CH₂Cl₂ / 20 °C

6: 100 percent / TBAF / tetrahydrofuran / 20 °C

With dmap; 2,6-di-tert-butyl-4-methyl-phenol; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; sodium hydrogencarbonate; triethylamine; chromium dichloride; nickel dichloride; In tetrahydrofuran; dichloromethane; toluene; 3: Kishi-Nozaki reaction / 4: intramolecular Diels-Alder reaction;
DOI:10.1016/S0040-4039(02)00536-1