(4aR,4bS,7S,8aS,10aR)-7-(Benzoyloxy)-<2,5-dihydroxy-3-methylbenzyl>-4a,4b,5,6,7,8,8a,9,10,10a-decahydro-2,4b,8,8,10a-pentamethylphenanthren-3(4H)-one

Base Information

Chemical Name:(4aR,4bS,7S,8aS,10aR)-7-(Benzoyloxy)-<2,5-dihydroxy-3-methylbenzyl>-4a,4b,5,6,7,8,8a,9,10,10a-decahydro-2,4b,8,8,10a-pentamethylphenanthren-3(4H)-one
CAS No.:149051-05-8
Molecular Formula:C₃₄H₄₂O₅
Molecular Weight:530.704
Hs Code.:

(4aR,4bS,7S,8aS,10aR)-7-(Benzoyloxy)-<2,5-dihydroxy-3-methylbenzyl>-4a,4b,5,6,7,8,8a,9,10,10a-decahydro-2,4b,8,8,10a-pentamethylphenanthren-3(4H)-one

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Chemical Property of (4aR,4bS,7S,8aS,10aR)-7-(Benzoyloxy)-<2,5-dihydroxy-3-methylbenzyl>-4a,4b,5,6,7,8,8a,9,10,10a-decahydro-2,4b,8,8,10a-pentamethylphenanthren-3(4H)-one

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Technology Process of (4aR,4bS,7S,8aS,10aR)-7-(Benzoyloxy)-<2,5-dihydroxy-3-methylbenzyl>-4a,4b,5,6,7,8,8a,9,10,10a-decahydro-2,4b,8,8,10a-pentamethylphenanthren-3(4H)-one

There total 22 articles about (4aR,4bS,7S,8aS,10aR)-7-(Benzoyloxy)-<2,5-dihydroxy-3-methylbenzyl>-4a,4b,5,6,7,8,8a,9,10,10a-decahydro-2,4b,8,8,10a-pentamethylphenanthren-3(4H)-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: 26.0%

: 149051-03-6
(4aR,4bS,7S,8aS,10aR)-7-(Benzoyloxy)-1-<2,5-bis(methoxymethoxy)-3-methylbenzyl>-4a,4b,5,6,7,8,8a,9,10,10a-decahydro-2,4b,8,8,10a-pentamethylphenanthren-3(4H)-one

: 149051-04-7
(1'S,2'S,4'aR,4'bS,7'S,8'aS,10'aR)-7'-(Benzoyloxy)-4a',4b',5',6',7',8',8a',9',10',10a'-decahydro-5-hydroxy-2',4b',7,8',8',10a'-hexamethylspiro-3'(4'H)-one

: 149051-05-8
(4aR,4bS,7S,8aS,10aR)-7-(Benzoyloxy)-<2,5-dihydroxy-3-methylbenzyl>-4a,4b,5,6,7,8,8a,9,10,10a-decahydro-2,4b,8,8,10a-pentamethylphenanthren-3(4H)-one

Guidance literature:: With boron tribromide; In dichloromethane; at -78 - -10 ℃; for 2.5h;

Reference yield:

: 106540-32-3
(3S)-3-t-butyldimethylsilyloxy-2,2,6-trimethylcyclohexanone

: 149051-05-8
(4aR,4bS,7S,8aS,10aR)-7-(Benzoyloxy)-<2,5-dihydroxy-3-methylbenzyl>-4a,4b,5,6,7,8,8a,9,10,10a-decahydro-2,4b,8,8,10a-pentamethylphenanthren-3(4H)-one

Guidance literature:: Multi-step reaction with 21 steps

1: 1.) Mg, 1,2-dibromoethane / 1.) THF, 25 deg C, 1 h, 2.) THF, r.t., 15 h

2: 98 percent / SOCl₂ / pyridine / 0.17 h / -10 °C

3: nBu₄NF / tetrahydrofuran / 1.) 40 deg C, 20 h, 2.) r.t., 48 h

4: KH / tetrahydrofuran / 1.) r.t., 0.5 h, 2.) r.t., 1 h

5: 99 percent / p-TsOH*H₂O / acetone; H₂O / 4 h / Heating

6: 79 percent / NaH, MeOH / 16 h / Heating

7: 18 percent / SnCl₄ / CH₂Cl₂; H₂O / 1.) 0 deg C, 1 h, 2.) r.t., 4 h

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

9: 1.) CuI / 1.) ether, -20 deg C, 10 min, 2.) ether, -78 deg C, 0.5 h; -20 deg C, 15 h

10: 88 percent / DIBAL / toluene / 0.5 h / -78 °C

11: Et₃N / CH₂Cl₂ / 0.5 h / -78 °C

12: LiBr / tetrahydrofuran; CH₂Cl₂ / 1 h / -20 °C

13: NaH, n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / 1.) 0 deg C, 15 min; 0 deg C, 30 min, 2.) -20 deg C, 15 h

14: 31 percent / SnCl₄ / CH₂Cl₂; H₂O / 2 h / 0 °C

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

16: 1.) CuI / 1.) ether, -20 deg C, 10 min, 2.) ether, -78 deg C, 0.5 h; -20 deg C, 15 h

17: 94 percent / DIBAL / toluene / 1 h / -78 °C

18: 99 percent / pyridine, DMAP / 0.5 h / 0 °C

19: 1.) n-BuLi, Me₃SnCl, 2.) LiCl / 2.) Pd(dba)2 / 1.) THF, hexane, -50 deg C, 0.5 h; -50 deg C, 3 h, 2.) DMF, 100 deg C, 4 h

20: 71 percent / CrO₃, 3,5-dimethylpyrazole / CH₂Cl₂ / 0.5 h / -20 °C

21: 26 percent / BBr₃ / CH₂Cl₂ / 2.5 h / -78 - -10 °C

With pyridine; 3,5-dimethyl-1H-pyrazole; chromium(VI) oxide; methanol; dmap; copper(l) iodide; n-butyllithium; thionyl chloride; trimethyltin(IV)chloride; tetrabutyl ammonium fluoride; boron tribromide; tin(IV) chloride; potassium hydride; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; magnesium; ethylene dibromide; triethylamine; lithium chloride; lithium bromide; bis(dibenzylideneacetone)-palladium⁽⁰⁾; In tetrahydrofuran; pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; dichloromethane; water; acetone; toluene;

Reference yield:

: 115333-56-7
(4aR,6S,8aS)-(+)-3,4,4a,5,6,7,8,8a-octahydro-6-benzyloxy-1-hydroxymethyl-2,5,5,8a-tetramethylnaphthalene

: 149051-05-8
(4aR,4bS,7S,8aS,10aR)-7-(Benzoyloxy)-<2,5-dihydroxy-3-methylbenzyl>-4a,4b,5,6,7,8,8a,9,10,10a-decahydro-2,4b,8,8,10a-pentamethylphenanthren-3(4H)-one

Guidance literature:: Multi-step reaction with 11 steps

1: Et₃N / CH₂Cl₂ / 0.5 h / -78 °C

2: LiBr / tetrahydrofuran; CH₂Cl₂ / 1 h / -20 °C

3: NaH, n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / 1.) 0 deg C, 15 min; 0 deg C, 30 min, 2.) -20 deg C, 15 h

4: 31 percent / SnCl₄ / CH₂Cl₂; H₂O / 2 h / 0 °C

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

6: 1.) CuI / 1.) ether, -20 deg C, 10 min, 2.) ether, -78 deg C, 0.5 h; -20 deg C, 15 h

7: 94 percent / DIBAL / toluene / 1 h / -78 °C

8: 99 percent / pyridine, DMAP / 0.5 h / 0 °C

9: 1.) n-BuLi, Me₃SnCl, 2.) LiCl / 2.) Pd(dba)2 / 1.) THF, hexane, -50 deg C, 0.5 h; -50 deg C, 3 h, 2.) DMF, 100 deg C, 4 h

10: 71 percent / CrO₃, 3,5-dimethylpyrazole / CH₂Cl₂ / 0.5 h / -20 °C

11: 26 percent / BBr₃ / CH₂Cl₂ / 2.5 h / -78 - -10 °C

With pyridine; 3,5-dimethyl-1H-pyrazole; chromium(VI) oxide; dmap; copper(l) iodide; n-butyllithium; trimethyltin(IV)chloride; boron tribromide; tin(IV) chloride; sodium hydride; diisobutylaluminium hydride; triethylamine; lithium chloride; lithium bromide; bis(dibenzylideneacetone)-palladium⁽⁰⁾; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; dichloromethane; water; toluene;