Methyl (4aR,4bS,7S,8aS,10aR)-7-(benzyloxy)-3,4,4a,4b,5,6,7,8,8a,9,10,10a-dodecahydro-2,4b,8,8,10a-pentamethylphenanthrene-1-carboxylate

Base Information

Chemical Name:Methyl (4aR,4bS,7S,8aS,10aR)-7-(benzyloxy)-3,4,4a,4b,5,6,7,8,8a,9,10,10a-dodecahydro-2,4b,8,8,10a-pentamethylphenanthrene-1-carboxylate
CAS No.:172788-46-4
Molecular Formula:C₂₈H₄₀O₃
Molecular Weight:424.624
Hs Code.:

Synonyms:Methyl (4aR,4bS,7S,8aS,10aR)-7-(benzyloxy)-3,4,4a,4b,5,6,7,8,8a,9,10,10a-dodecahydro-2,4b,8,8,10a-pentamethylphenanthrene-1-carboxylate

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Chemical Property of Methyl (4aR,4bS,7S,8aS,10aR)-7-(benzyloxy)-3,4,4a,4b,5,6,7,8,8a,9,10,10a-dodecahydro-2,4b,8,8,10a-pentamethylphenanthrene-1-carboxylate

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Technology Process of Methyl (4aR,4bS,7S,8aS,10aR)-7-(benzyloxy)-3,4,4a,4b,5,6,7,8,8a,9,10,10a-dodecahydro-2,4b,8,8,10a-pentamethylphenanthrene-1-carboxylate

There total 15 articles about Methyl (4aR,4bS,7S,8aS,10aR)-7-(benzyloxy)-3,4,4a,4b,5,6,7,8,8a,9,10,10a-dodecahydro-2,4b,8,8,10a-pentamethylphenanthrene-1-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:

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

: 172788-46-4
Methyl (4aR,4bS,7S,8aS,10aR)-7-(benzyloxy)-3,4,4a,4b,5,6,7,8,8a,9,10,10a-dodecahydro-2,4b,8,8,10a-pentamethylphenanthrene-1-carboxylate

Guidance literature:: Multi-step reaction with 16 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

With methanol; copper(l) iodide; n-butyllithium; thionyl chloride; tetrabutyl ammonium fluoride; tin(IV) chloride; potassium hydride; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; magnesium; ethylene dibromide; triethylamine; lithium bromide; 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

: 172788-46-4
Methyl (4aR,4bS,7S,8aS,10aR)-7-(benzyloxy)-3,4,4a,4b,5,6,7,8,8a,9,10,10a-dodecahydro-2,4b,8,8,10a-pentamethylphenanthrene-1-carboxylate

Guidance literature:: Multi-step reaction with 6 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

With copper(l) iodide; n-butyllithium; tin(IV) chloride; sodium hydride; triethylamine; lithium bromide; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; dichloromethane; water;

Reference yield:

: 115404-48-3
(3S,4aR,8aS)-3-Benzyloxy-8-bromomethyl-4,4,7,8a-tetramethyl-1,2,3,4,4a,5,6,8a-octahydro-naphthalene

: 172788-46-4
Methyl (4aR,4bS,7S,8aS,10aR)-7-(benzyloxy)-3,4,4a,4b,5,6,7,8,8a,9,10,10a-dodecahydro-2,4b,8,8,10a-pentamethylphenanthrene-1-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1: 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

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

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

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

With copper(l) iodide; n-butyllithium; tin(IV) chloride; sodium hydride; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; dichloromethane; water;