(3S,4S,12bS)-1,2,3,4-Tetrahydro-3,5-dihydroxy-4-(hydroxymethyl)-8,11-dimethoxy-12b-methyl-6(12bH)benzanthracenone

Base Information

• Chemical Name: (3S,4S,12bS)-1,2,3,4-Tetrahydro-3,5-dihydroxy-4-(hydroxymethyl)-8,11-dimethoxy-12b-methyl-6(12bH)benz
• Molecular Formula: C₂₂H₂₄O₆
• Molecular Weight: 384.429

Synonyms:

Chemical Property of (3S,4S,12bS)-1,2,3,4-Tetrahydro-3,5-dihydroxy-4-(hydroxymethyl)-8,11-dimethoxy-12b-methyl-6(12bH)benz

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

There total 12 articles about (3S,4S,12bS)-1,2,3,4-Tetrahydro-3,5-dihydroxy-4-(hydroxymethyl)-8,11-dimethoxy-12b-methyl-6(12bH)benzanthracenone 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:

(4aR,5S,8aR)-3,4,4a,5,8,8a-hexahydro-5-(hydroxymethyl)-8a-methyl-1,6-(2H,7H)-naphthalenedione 1-ethylene acetal (117439-20-0) → (3S,4S,12bS)-1,2,3,4-Tetrahydro-3,5-dihydroxy-4-(hydroxymethyl)-8,11-dimethoxy-12b-methyl-6(12bH)benzanthracenone (117439-30-2)

Guidance literature:

Multi-step reaction with 10 steps

1: 92 percent / lithium tri-sec-butylborohydride / tetrahydrofuran / 0.33 h / 0 °C

2: 98 percent / p-toluenesulfonic acid monohydrate / H₂O / 3 h / Ambient temperature

3: 13.0 g / ethanol / 4 h / Heating

4: methyllithium / diethyl ether; tetrahydrofuran / 1 h / Ambient temperature

5: 86 percent / p-toluenesulfonic acid, triethylamine / 4 h / Ambient temperature

6: 63 percent / chromium(VI) oxide, 3,5-dimethylpyrazole / CH₂Cl₂ / 2.5 h / -20 °C

7: 33 percent / benzene / 20 h / 210 - 215 °C

8: 89 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) / benzene / 3.5 h / Heating

9: 90 percent / potassium tert-butoxide, tert-butyl alcohol, oxygen / 4 h / Ambient temperature

10: 0.071 g / 60 percent aq. acetic acid / 0.5 h / Ambient temperature

With 3,5-dimethyl-1H-pyrazole; chromium(VI) oxide; potassium tert-butylate; methyllithium; oxygen; L-Selectride; toluene-4-sulfonic acid; acetic acid; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; tert-butyl alcohol; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; water; benzene;

DOI:10.1021/ja00233a026

Reference yield:

(1S,2S,4aS,8aR)-(-)-1,2,3,4,4a,7,8,8a-octahydro-1-(hydroxymethyl)-4a-methyl-2-naphthalenol (117439-23-3) → (3S,4S,12bS)-1,2,3,4-Tetrahydro-3,5-dihydroxy-4-(hydroxymethyl)-8,11-dimethoxy-12b-methyl-6(12bH)benzanthracenone (117439-30-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 86 percent / p-toluenesulfonic acid, triethylamine / 4 h / Ambient temperature

2: 63 percent / chromium(VI) oxide, 3,5-dimethylpyrazole / CH₂Cl₂ / 2.5 h / -20 °C

3: 33 percent / benzene / 20 h / 210 - 215 °C

4: 89 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) / benzene / 3.5 h / Heating

5: 90 percent / potassium tert-butoxide, tert-butyl alcohol, oxygen / 4 h / Ambient temperature

6: 0.071 g / 60 percent aq. acetic acid / 0.5 h / Ambient temperature

With 3,5-dimethyl-1H-pyrazole; chromium(VI) oxide; potassium tert-butylate; oxygen; toluene-4-sulfonic acid; acetic acid; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; tert-butyl alcohol; In dichloromethane; benzene;

DOI:10.1021/ja00233a026

Reference yield:

(4aR,5S,6S,8aR)-(+)-3,4,4a,5,6,7,8,8a-octahydro-6-hydroxy-5-(hydroxymethyl)-8a-methyl-1-(2H)-naphthalenone 1-ethylene acetal (117439-21-1) → (3S,4S,12bS)-1,2,3,4-Tetrahydro-3,5-dihydroxy-4-(hydroxymethyl)-8,11-dimethoxy-12b-methyl-6(12bH)benzanthracenone (117439-30-2)

Guidance literature:

Multi-step reaction with 9 steps

1: 98 percent / p-toluenesulfonic acid monohydrate / H₂O / 3 h / Ambient temperature

2: 13.0 g / ethanol / 4 h / Heating

3: methyllithium / diethyl ether; tetrahydrofuran / 1 h / Ambient temperature

4: 86 percent / p-toluenesulfonic acid, triethylamine / 4 h / Ambient temperature

5: 63 percent / chromium(VI) oxide, 3,5-dimethylpyrazole / CH₂Cl₂ / 2.5 h / -20 °C

6: 33 percent / benzene / 20 h / 210 - 215 °C

7: 89 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) / benzene / 3.5 h / Heating

8: 90 percent / potassium tert-butoxide, tert-butyl alcohol, oxygen / 4 h / Ambient temperature

9: 0.071 g / 60 percent aq. acetic acid / 0.5 h / Ambient temperature

With 3,5-dimethyl-1H-pyrazole; chromium(VI) oxide; potassium tert-butylate; methyllithium; oxygen; toluene-4-sulfonic acid; acetic acid; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; tert-butyl alcohol; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; water; benzene;

DOI:10.1021/ja00233a026

upstream raw materials:

(3S,4S,12bS)-1,2,3,4-tetrahydro-3,5-dihydroxy-4-(hydroxymethyl)-8,11-dimethoxy-12b-methyl-6(12bH)-benzoanthracenone acetonide

(4aR,5S,8aR)-3,4,4a,5,8,8a-hexahydro-5-(hydroxymethyl)-8a-methyl-1,6-(2H,7H)-naphthalenedione 1-ethylene acetal

(1S,2S,4aS,8aR)-(-)-1,2,3,4,4a,7,8,8a-octahydro-1-(hydroxymethyl)-4a-methyl-2-naphthalenol

(4aR,5S,6S,8aR)-(+)-3,4,4a,5,6,7,8,8a-octahydro-6-hydroxy-5-(hydroxymethyl)-8a-methyl-1-(2H)-naphthalenone 1-ethylene acetal

Downstream raw materials:

(+)-halenaquinone

halenaquinol

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