(4aR*,4bS*,8aS*,10aR*)-1-<2,5-dihydroxy-3-methylbenzyl>-3,4,4a,4b,5,6,7,8,8a,9,10,10a-dodecahydro-2,4b,8,8,10a-pentamethylphenanthren-3-one

Base Information

• Chemical Name: (4aR*,4bS*,8aS*,10aR*)-1-<2,5-dihydroxy-3-methylbenzyl>-3,4,4a,4b,5,6,7,8,8a,9,10,10a-dodecahydro-2,4b,8,8,10a-pentamethylphenanthren-3-one
• CAS No.: 133909-17-8
• Molecular Formula: C₂₇H₃₈O₃
• Molecular Weight: 410.597
• Mol file: 133909-17-8.mol

Synonyms:

Chemical Property of (4aR*,4bS*,8aS*,10aR*)-1-<2,5-dihydroxy-3-methylbenzyl>-3,4,4a,4b,5,6,7,8,8a,9,10,10a-dodecahydro-2,4b,8,8,10a-pentamethylphenanthren-3-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4aR*,4bS*,8aS*,10aR*)-1-<2,5-dihydroxy-3-methylbenzyl>-3,4,4a,4b,5,6,7,8,8a,9,10,10a-dodecahydro-2,4b,8,8,10a-pentamethylphenanthren-3-one

There total 13 articles about (4aR*,4bS*,8aS*,10aR*)-1-<2,5-dihydroxy-3-methylbenzyl>-3,4,4a,4b,5,6,7,8,8a,9,10,10a-dodecahydro-2,4b,8,8,10a-pentamethylphenanthren-3-one 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:

(4aS*,8aS*)-3,4,4a,5,6,7,8,8a-octahydro-2,5,5,8a-tetra-methyl-trans-naphthalene-1-methanol (94370-10-2,124377-31-7,83043-63-4) → (4aR*,4bS*,8aS*,10aR*)-1-<2,5-dihydroxy-3-methylbenzyl>-3,4,4a,4b,5,6,7,8,8a,9,10,10a-dodecahydro-2,4b,8,8,10a-pentamethylphenanthren-3-one (133909-17-8)

Guidance literature:

Multi-step reaction with 10 steps

1: 1.) methanesulfonyl chloride, triethylamine, 2.) LiBr / 1.) dichloromethane, -78 deg C, 30 min, 2.) THF, -20 deg C, 1 h

3: 79 percent / stannic chloride / CH₂Cl₂; H₂O / 1.) 0 deg C, 1 h, 2.) r.t., 20 h

4: 1.) NaH / 1.) THF, 1 h, reflux, 2.) 1 h, r.t.

5: 1.) CuI / 1.) ether, 10 min, -10 deg C, 2.) ether, -78 deg C, 1 h -> -20 deg C, 16 h

6: 95 percent / diisobutylaluminium hydride (DIBAL) / toluene / 1 h / -78 °C

7: 1.) methaneslfonyl chloride, triethylamine, 2.) LiBr / 1.) dichloromethane, -78 deg C, 30 min, 2.) THF, -20 deg C, 1 h

9: 81 percent / CrO₃, 3,5-dimethylpyrazole / CH₂Cl₂ / 0.17 h / -20 °C

10: 1.) BBr₃, 2.) H₂O / 1.) CH₂Cl₂, -78 deg C -> -10 deg C, 3 h, 2.) r.t., 12 h

With 3,5-dimethyl-1H-pyrazole; chromium(VI) oxide; copper(l) iodide; water; boron tribromide; sodium hydride; diisobutylaluminium hydride; methanesulfonyl chloride; triethylamine; lithium bromide; tin(IV) chloride; In dichloromethane; water; toluene;

Reference yield:

(+/-)-8-oxo-12-nordriman-11-acid methyl ester (59684-77-4,65794-68-5,115304-46-6,131831-72-6,133102-26-8,49749-46-4,141317-75-1) → (4aR*,4bS*,8aS*,10aR*)-1-<2,5-dihydroxy-3-methylbenzyl>-3,4,4a,4b,5,6,7,8,8a,9,10,10a-dodecahydro-2,4b,8,8,10a-pentamethylphenanthren-3-one (133909-17-8)

Guidance literature:

Multi-step reaction with 13 steps

1: 1.) NaH / 1.)THF, 1 h, reflux, 2.) 1 h, r.t.

2: 1.) CuI / 1.) ether, 10 min, -10 deg C, 2.) ether, -78 deg C, 1 h, -20 deg C, 16 h

3: 91 percent / diisobutylaluminium hydride (DIBAL) / toluene / 1 h / -78 °C

4: 1.) methanesulfonyl chloride, triethylamine, 2.) LiBr / 1.) dichloromethane, -78 deg C, 30 min, 2.) THF, -20 deg C, 1 h

6: 79 percent / stannic chloride / CH₂Cl₂; H₂O / 1.) 0 deg C, 1 h, 2.) r.t., 20 h

7: 1.) NaH / 1.) THF, 1 h, reflux, 2.) 1 h, r.t.

8: 1.) CuI / 1.) ether, 10 min, -10 deg C, 2.) ether, -78 deg C, 1 h -> -20 deg C, 16 h

9: 95 percent / diisobutylaluminium hydride (DIBAL) / toluene / 1 h / -78 °C

10: 1.) methaneslfonyl chloride, triethylamine, 2.) LiBr / 1.) dichloromethane, -78 deg C, 30 min, 2.) THF, -20 deg C, 1 h

12: 81 percent / CrO₃, 3,5-dimethylpyrazole / CH₂Cl₂ / 0.17 h / -20 °C

13: 1.) BBr₃, 2.) H₂O / 1.) CH₂Cl₂, -78 deg C -> -10 deg C, 3 h, 2.) r.t., 12 h

With 3,5-dimethyl-1H-pyrazole; chromium(VI) oxide; copper(l) iodide; water; boron tribromide; sodium hydride; diisobutylaluminium hydride; methanesulfonyl chloride; triethylamine; lithium bromide; tin(IV) chloride; In dichloromethane; water; toluene;

Reference yield:

(4aS,8aS)-8-Bromomethyl-4,4,7,8a-tetramethyl-1,2,3,4,4a,5,6,8a-octahydro-naphthalene (39052-34-1) → (4aR*,4bS*,8aS*,10aR*)-1-<2,5-dihydroxy-3-methylbenzyl>-3,4,4a,4b,5,6,7,8,8a,9,10,10a-dodecahydro-2,4b,8,8,10a-pentamethylphenanthren-3-one (133909-17-8)

Guidance literature:

Multi-step reaction with 9 steps

2: 79 percent / stannic chloride / CH₂Cl₂; H₂O / 1.) 0 deg C, 1 h, 2.) r.t., 20 h

3: 1.) NaH / 1.) THF, 1 h, reflux, 2.) 1 h, r.t.

4: 1.) CuI / 1.) ether, 10 min, -10 deg C, 2.) ether, -78 deg C, 1 h -> -20 deg C, 16 h

5: 95 percent / diisobutylaluminium hydride (DIBAL) / toluene / 1 h / -78 °C

6: 1.) methaneslfonyl chloride, triethylamine, 2.) LiBr / 1.) dichloromethane, -78 deg C, 30 min, 2.) THF, -20 deg C, 1 h

8: 81 percent / CrO₃, 3,5-dimethylpyrazole / CH₂Cl₂ / 0.17 h / -20 °C

9: 1.) BBr₃, 2.) H₂O / 1.) CH₂Cl₂, -78 deg C -> -10 deg C, 3 h, 2.) r.t., 12 h

With 3,5-dimethyl-1H-pyrazole; chromium(VI) oxide; copper(l) iodide; water; boron tribromide; sodium hydride; diisobutylaluminium hydride; methanesulfonyl chloride; triethylamine; lithium bromide; tin(IV) chloride; In dichloromethane; water; toluene;

upstream raw materials:

(4aR*.4bS*,8aS*,10aR*)-1-<2,5-bis(methoxymethoxy)-3-methylbenzyl>-3,4,4a,4b,5,6,7,8,8a,9,10,10a-dodecahydro-2,4b,8,8,10a-pentamethylphenanthrene-3-one

(4aS*,8aS*)-3,4,4a,5,6,7,8,8a-octahydro-2,5,5,8a-tetra-methyl-trans-naphthalene-1-methanol

(+/-)-8-oxo-12-nordriman-11-acid methyl ester

(4aS,8aS)-8-Bromomethyl-4,4,7,8a-tetramethyl-1,2,3,4,4a,5,6,8a-octahydro-naphthalene