(1R,2R,3S,3aR,8bS)-methyl 1,8b-dihydroxy-6,8-dimethoxy-3-phenyl-3a-p-tolyl-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan-2-carboxylate

Base Information

• Chemical Name: (1R,2R,3S,3aR,8bS)-methyl 1,8b-dihydroxy-6,8-dimethoxy-3-phenyl-3a-p-tolyl-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan-2-carboxylate
• CAS No.: 1139261-87-2
• Molecular Formula: C₂₈H₂₈O₇
• Molecular Weight: 476.526

Synonyms:

Chemical Property of (1R,2R,3S,3aR,8bS)-methyl 1,8b-dihydroxy-6,8-dimethoxy-3-phenyl-3a-p-tolyl-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan-2-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2R,3S,3aR,8bS)-methyl 1,8b-dihydroxy-6,8-dimethoxy-3-phenyl-3a-p-tolyl-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan-2-carboxylate

There total 15 articles about (1R,2R,3S,3aR,8bS)-methyl 1,8b-dihydroxy-6,8-dimethoxy-3-phenyl-3a-p-tolyl-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan-2-carboxylate 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:

5,7-dihydroxy-2-phenyl-chromen-4-one (480-40-0) → (1R,2R,3S,3aR,8bS)-methyl 1,8b-dihydroxy-6,8-dimethoxy-3-phenyl-3a-p-tolyl-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan-2-carboxylate (1139261-87-2)

Guidance literature:

Multi-step reaction with 15 steps

1.1: potassium carbonate / acetone / 3 h / 60 °C / Inert atmosphere

2.1: acetone / 72 h / 40 °C / Inert atmosphere

3.1: pyridine / water; diethylene glycol / 2 h / 100 °C / Inert atmosphere; Alkaline conditions

4.1: triethylamine / dichloromethane / 1 h / 0 °C / Inert atmosphere

5.1: sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid / dichloromethane / 4 h / 0 - 20 °C / Inert atmosphere

5.2: 6 h / Inert atmosphere; Reflux

6.1: dmap; triethylamine / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere

7.1: lithium hexamethyldisilazane / tetrahydrofuran / 2.5 h / -70 - -20 °C / Inert atmosphere

8.1: sulfuric acid; acetic acid / 8 h / 75 °C / Inert atmosphere

8.2: 2 h / 20 °C / Inert atmosphere

9.1: water; sodium hydroxide / ethanol / 1 h / 80 °C / Inert atmosphere

10.1: methanol; dichloromethane; acetonitrile / 3 h / 0 - 5 °C / Inert atmosphere; UV-irradiation

10.2: 1 h / 60 °C / Inert atmosphere

11.1: acetic acid; tetramethylammonium triacetoxyborohydride / acetonitrile / 48 h / Inert atmosphere

12.1: LUX Cellulose-2 / methanol / Inert atmosphere; Resolution of racemate; Supercritical conditions

13.1: palladium diacetate; caesium carbonate; XPhos / toluene / 100 °C / Inert atmosphere

14.1: 5%-palladium/activated carbon; hydrogen / tetrahydrofuran / 18 h / 20 °C / Inert atmosphere

15.1: methanol; toluene / 4 h / Inert atmosphere

With pyridine; dmap; sulfuric acid; 5%-palladium/activated carbon; water; hydrogen; palladium diacetate; sodium hydrogencarbonate; potassium carbonate; caesium carbonate; acetic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; sodium hydroxide; lithium hexamethyldisilazane; tetramethylammonium triacetoxyborohydride; XPhos; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; acetone; toluene; acetonitrile; diethylene glycol; 5.1: |Rubottom Oxidation / 5.2: |Rubottom Oxidation / 7.1: |Baker-Venkataraman Rearrangement;

DOI:10.1021/jm3011542

Reference yield:

7-(benzyloxy)-5-hydroxy-2-phenyl-4H-chromen-4-one (110506-85-9) → (1R,2R,3S,3aR,8bS)-methyl 1,8b-dihydroxy-6,8-dimethoxy-3-phenyl-3a-p-tolyl-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan-2-carboxylate (1139261-87-2)

Guidance literature:

Multi-step reaction with 14 steps

1.1: acetone / 72 h / 40 °C / Inert atmosphere

2.1: pyridine / water; diethylene glycol / 2 h / 100 °C / Inert atmosphere; Alkaline conditions

3.1: triethylamine / dichloromethane / 1 h / 0 °C / Inert atmosphere

4.1: sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid / dichloromethane / 4 h / 0 - 20 °C / Inert atmosphere

4.2: 6 h / Inert atmosphere; Reflux

5.1: dmap; triethylamine / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere

6.1: lithium hexamethyldisilazane / tetrahydrofuran / 2.5 h / -70 - -20 °C / Inert atmosphere

7.1: sulfuric acid; acetic acid / 8 h / 75 °C / Inert atmosphere

7.2: 2 h / 20 °C / Inert atmosphere

8.1: water; sodium hydroxide / ethanol / 1 h / 80 °C / Inert atmosphere

9.1: methanol; dichloromethane; acetonitrile / 3 h / 0 - 5 °C / Inert atmosphere; UV-irradiation

9.2: 1 h / 60 °C / Inert atmosphere

10.1: acetic acid; tetramethylammonium triacetoxyborohydride / acetonitrile / 48 h / Inert atmosphere

11.1: LUX Cellulose-2 / methanol / Inert atmosphere; Resolution of racemate; Supercritical conditions

12.1: palladium diacetate; caesium carbonate; XPhos / toluene / 100 °C / Inert atmosphere

13.1: 5%-palladium/activated carbon; hydrogen / tetrahydrofuran / 18 h / 20 °C / Inert atmosphere

14.1: methanol; toluene / 4 h / Inert atmosphere

With pyridine; dmap; sulfuric acid; 5%-palladium/activated carbon; water; hydrogen; palladium diacetate; sodium hydrogencarbonate; caesium carbonate; acetic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; sodium hydroxide; lithium hexamethyldisilazane; tetramethylammonium triacetoxyborohydride; XPhos; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; acetone; toluene; acetonitrile; diethylene glycol; 4.1: |Rubottom Oxidation / 4.2: |Rubottom Oxidation / 6.1: |Baker-Venkataraman Rearrangement;

DOI:10.1021/jm3011542

Reference yield:

1-(4-(benzyloxy)-2-hydroxy-6-methoxyphenyl)ethanone (681294-57-5) → (1R,2R,3S,3aR,8bS)-methyl 1,8b-dihydroxy-6,8-dimethoxy-3-phenyl-3a-p-tolyl-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan-2-carboxylate (1139261-87-2)

Guidance literature:

Multi-step reaction with 13 steps

1.1: pyridine / water; diethylene glycol / 2 h / 100 °C / Inert atmosphere; Alkaline conditions

2.1: triethylamine / dichloromethane / 1 h / 0 °C / Inert atmosphere

3.1: sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid / dichloromethane / 4 h / 0 - 20 °C / Inert atmosphere

3.2: 6 h / Inert atmosphere; Reflux

4.1: dmap; triethylamine / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere

5.1: lithium hexamethyldisilazane / tetrahydrofuran / 2.5 h / -70 - -20 °C / Inert atmosphere

6.1: sulfuric acid; acetic acid / 8 h / 75 °C / Inert atmosphere

6.2: 2 h / 20 °C / Inert atmosphere

7.1: water; sodium hydroxide / ethanol / 1 h / 80 °C / Inert atmosphere

8.1: methanol; dichloromethane; acetonitrile / 3 h / 0 - 5 °C / Inert atmosphere; UV-irradiation

8.2: 1 h / 60 °C / Inert atmosphere

9.1: acetic acid; tetramethylammonium triacetoxyborohydride / acetonitrile / 48 h / Inert atmosphere

10.1: LUX Cellulose-2 / methanol / Inert atmosphere; Resolution of racemate; Supercritical conditions

11.1: palladium diacetate; caesium carbonate; XPhos / toluene / 100 °C / Inert atmosphere

12.1: 5%-palladium/activated carbon; hydrogen / tetrahydrofuran / 18 h / 20 °C / Inert atmosphere

13.1: methanol; toluene / 4 h / Inert atmosphere

With pyridine; dmap; sulfuric acid; 5%-palladium/activated carbon; water; hydrogen; palladium diacetate; sodium hydrogencarbonate; caesium carbonate; acetic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; sodium hydroxide; lithium hexamethyldisilazane; tetramethylammonium triacetoxyborohydride; XPhos; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; toluene; acetonitrile; diethylene glycol; 3.1: |Rubottom Oxidation / 3.2: |Rubottom Oxidation / 5.1: |Baker-Venkataraman Rearrangement;

DOI:10.1021/jm3011542

upstream raw materials:

C₂₇H₂₆O₇

diazomethyl-trimethyl-silane

5,7-dihydroxy-2-phenyl-chromen-4-one

7-(benzyloxy)-5-hydroxy-2-phenyl-4H-chromen-4-one

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