(1R,4aS,4bR,8aS,9R,10aS)-8a-<(Benzyloxy)methyl>-9-(2-bromo-1(S)-ethoxyethoxy)-1,4,4a,4b,5,6,7,8,8a,9,10,10a-dodecahydro-1,4a-dimethylphenanthren-7-one

Base Information

• Chemical Name: (1R,4aS,4bR,8aS,9R,10aS)-8a-<(Benzyloxy)methyl>-9-(2-bromo-1(S)-ethoxyethoxy)-1,4,4a,4b,5,6,7,8,8a,9,10,10a-dodecahydro-1,4a-dimethylphenanthren-7-one
• CAS No.: 155028-15-2
• Molecular Formula: C₂₈H₃₉BrO₄
• Molecular Weight: 519.519
• Mol file: 155028-15-2.mol

Synonyms:(1R,4aS,4bR,8aS,9R,10aS)-8a-<(Benzyloxy)methyl>-9-(2-bromo-1(S)-ethoxyethoxy)-1,4,4a,4b,5,6,7,8,8a,9,10,10a-dodecahydro-1,4a-dimethylphenanthren-7-one

Chemical Property of (1R,4aS,4bR,8aS,9R,10aS)-8a-<(Benzyloxy)methyl>-9-(2-bromo-1(S)-ethoxyethoxy)-1,4,4a,4b,5,6,7,8,8a,9,10,10a-dodecahydro-1,4a-dimethylphenanthren-7-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,4aS,4bR,8aS,9R,10aS)-8a-<(Benzyloxy)methyl>-9-(2-bromo-1(S)-ethoxyethoxy)-1,4,4a,4b,5,6,7,8,8a,9,10,10a-dodecahydro-1,4a-dimethylphenanthren-7-one

There total 15 articles about (1R,4aS,4bR,8aS,9R,10aS)-8a-<(Benzyloxy)methyl>-9-(2-bromo-1(S)-ethoxyethoxy)-1,4,4a,4b,5,6,7,8,8a,9,10,10a-dodecahydro-1,4a-dimethylphenanthren-7-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:

(S)-(-)-2,3,4,4a,9,10-hexahydro-7-methoxy-1,4a-dimethyl-2-oxophenanthrene (89460-69-5) → (1R,4aS,4bR,8aS,9R,10aS)-8a-<(Benzyloxy)methyl>-9-(2-bromo-1(S)-ethoxyethoxy)-1,4,4a,4b,5,6,7,8,8a,9,10,10a-dodecahydro-1,4a-dimethylphenanthren-7-one (155028-15-2)

Guidance literature:

Multi-step reaction with 15 steps

1: Li, NH₃, t-BuOH / tetrahydrofuran / 2.5 h / -33 °C

2: Et₃N / CH₂Cl₂ / 0.83 h / -20 - -5 °C

3: PPTS / CH₂Cl₂ / 3.5 h / Ambient temperature

4: Oxone, NaHCO₃ / dioxane; tetrahydrofuran; H₂O / 2.5 h / 0 °C

5: 73.6 percent / imidazole / dimethylformamide / 72 h / Ambient temperature

6: NaBH₄ / ethanol / 5.5 h / Heating

7: 30percent aq. H₂O₂, NaHCO₃ / tetrahydrofuran / 36 h / Ambient temperature

8: 87 percent / KCN, 18-crown-6 ether / benzene; toluene / 24 h / Ambient temperature

9: Et₃N / CH₂Cl₂ / 1.5 h / 0 °C

10: DIBAL-H / diethyl ether; hexane / 1 h / 0 °C

11: DIBAL-H / diethyl ether; hexane / 1 h / -78 °C

12: NaH, (n-Bu)4NI / tetrahydrofuran / 45 h

13: 10percent aq. HCl / 20 h / Ambient temperature

14: 95.5 percent / (n-Bu)4NF / tetrahydrofuran / Ambient temperature

15: 1.) Br₂, 2.) dimethylaniline / 1.) -25 deg C, 30 min, 2.) CH₂Cl₂, r.t., 2.5 h

With 1H-imidazole; hydrogenchloride; potassium cyanide; Oxone; sodium tetrahydroborate; 18-crown-6 ether; tetrabutyl ammonium fluoride; ammonia; dihydrogen peroxide; bromine; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; lithium; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; triethylamine; 2,3-Dimethylaniline; tert-butyl alcohol; In tetrahydrofuran; 1,4-dioxane; diethyl ether; ethanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; benzene;

DOI:10.1021/jo00081a008

Reference yield:

(1S,2S,4aS,10aS)-1,2,3,4,4a,5,8,9,10,10a-decahydro-2-hydroxy-7-methoxy-1,4a-dimethylphenanthrene (155155-26-3) → (1R,4aS,4bR,8aS,9R,10aS)-8a-<(Benzyloxy)methyl>-9-(2-bromo-1(S)-ethoxyethoxy)-1,4,4a,4b,5,6,7,8,8a,9,10,10a-dodecahydro-1,4a-dimethylphenanthren-7-one (155028-15-2)

Guidance literature:

Multi-step reaction with 14 steps

1: Et₃N / CH₂Cl₂ / 0.83 h / -20 - -5 °C

2: PPTS / CH₂Cl₂ / 3.5 h / Ambient temperature

3: Oxone, NaHCO₃ / dioxane; tetrahydrofuran; H₂O / 2.5 h / 0 °C

4: 73.6 percent / imidazole / dimethylformamide / 72 h / Ambient temperature

5: NaBH₄ / ethanol / 5.5 h / Heating

6: 30percent aq. H₂O₂, NaHCO₃ / tetrahydrofuran / 36 h / Ambient temperature

7: 87 percent / KCN, 18-crown-6 ether / benzene; toluene / 24 h / Ambient temperature

8: Et₃N / CH₂Cl₂ / 1.5 h / 0 °C

9: DIBAL-H / diethyl ether; hexane / 1 h / 0 °C

10: DIBAL-H / diethyl ether; hexane / 1 h / -78 °C

11: NaH, (n-Bu)4NI / tetrahydrofuran / 45 h

12: 10percent aq. HCl / 20 h / Ambient temperature

13: 95.5 percent / (n-Bu)4NF / tetrahydrofuran / Ambient temperature

14: 1.) Br₂, 2.) dimethylaniline / 1.) -25 deg C, 30 min, 2.) CH₂Cl₂, r.t., 2.5 h

With 1H-imidazole; hydrogenchloride; potassium cyanide; Oxone; sodium tetrahydroborate; 18-crown-6 ether; tetrabutyl ammonium fluoride; dihydrogen peroxide; bromine; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; triethylamine; 2,3-Dimethylaniline; In tetrahydrofuran; 1,4-dioxane; diethyl ether; ethanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; benzene;

DOI:10.1021/jo00081a008

Reference yield:

(1S,2S,4aS,4bR,10aS)-1,2,3,4,4a,4b,5,6,10,10a-decahydro-2-(methanesulfonyl)-7-methoxy-1,4a-dimethylphenanthrene (155028-01-6) → (1R,4aS,4bR,8aS,9R,10aS)-8a-<(Benzyloxy)methyl>-9-(2-bromo-1(S)-ethoxyethoxy)-1,4,4a,4b,5,6,7,8,8a,9,10,10a-dodecahydro-1,4a-dimethylphenanthren-7-one (155028-15-2)

Guidance literature:

Multi-step reaction with 12 steps

1: Oxone, NaHCO₃ / dioxane; tetrahydrofuran; H₂O / 2.5 h / 0 °C

2: 73.6 percent / imidazole / dimethylformamide / 72 h / Ambient temperature

3: NaBH₄ / ethanol / 5.5 h / Heating

4: 30percent aq. H₂O₂, NaHCO₃ / tetrahydrofuran / 36 h / Ambient temperature

5: 87 percent / KCN, 18-crown-6 ether / benzene; toluene / 24 h / Ambient temperature

6: Et₃N / CH₂Cl₂ / 1.5 h / 0 °C

7: DIBAL-H / diethyl ether; hexane / 1 h / 0 °C

8: DIBAL-H / diethyl ether; hexane / 1 h / -78 °C

9: NaH, (n-Bu)4NI / tetrahydrofuran / 45 h

10: 10percent aq. HCl / 20 h / Ambient temperature

11: 95.5 percent / (n-Bu)4NF / tetrahydrofuran / Ambient temperature

12: 1.) Br₂, 2.) dimethylaniline / 1.) -25 deg C, 30 min, 2.) CH₂Cl₂, r.t., 2.5 h

With 1H-imidazole; hydrogenchloride; potassium cyanide; Oxone; sodium tetrahydroborate; 18-crown-6 ether; tetrabutyl ammonium fluoride; dihydrogen peroxide; bromine; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; triethylamine; 2,3-Dimethylaniline; In tetrahydrofuran; 1,4-dioxane; diethyl ether; ethanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; benzene;

DOI:10.1021/jo00081a008

upstream raw materials:

ethyl vinyl ether

(1R,4aS,4bR,8aS,9R,10aS)-8aβ-<(Benzyloxy)methyl>-1,4,4a,4b,5,6,7,8,8a,9,10,10a-dodecahydro-9α-hydroxy-1α,4aβ-dimethylphenanthren-7-one

(S)-(-)-2,3,4,4a,9,10-hexahydro-7-methoxy-1,4a-dimethyl-2-oxophenanthrene

(1S,2S,4aS,10aS)-1,2,3,4,4a,5,8,9,10,10a-decahydro-2-hydroxy-7-methoxy-1,4a-dimethylphenanthrene

Downstream raw materials:

(4R,5S,7R,8R,9R,10S,12S,14R,16S)-20-(Methanesulfonyl)-16-ethoxy-13-oxo-12-(phenylseleno)-21-norpicras-2-ene

(4R,5S,7R,8R,9R,10S,14R,16S)-20-<(Benzyloxy)methyl>-13-<(tert-butyldimethylsilyl)oxy>-16-ethoxy-21-norpicras-2,12-diene

(4R,5S,7R,8R,9R,10S,12R,13R,14R,16S)-13,20-Epoxy-16-ethoxy-12-(phenylseleno)-21-nitrilopicrasa-2-ene

(4R,5S,7R,8R,9R,10S,14R,16S)-20-<(Benzyloxy)methyl>-16-ethoxy-13-oxo-21-norpicras-2-ene