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

Base Information

• Chemical Name: (4R,5S,7R,8R,9R,10S,12S,14R,16S)-20-(Methanesulfonyl)-16-ethoxy-13-oxo-12-(phenylseleno)-21-norpicras-2-ene
• CAS No.: 155039-11-5
• Molecular Formula: C₂₈H₃₈O₆SSe
• Molecular Weight: 581.632
• Mol file: 155039-11-5.mol

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 19 articles about (4R,5S,7R,8R,9R,10S,12S,14R,16S)-20-(Methanesulfonyl)-16-ethoxy-13-oxo-12-(phenylseleno)-21-norpicras-2-ene 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) → (4R,5S,7R,8R,9R,10S,12S,14R,16S)-20-(Methanesulfonyl)-16-ethoxy-13-oxo-12-(phenylseleno)-21-norpicras-2-ene (155039-11-5)

Guidance literature:

Multi-step reaction with 20 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

16: 89.6 percent / t-BuOK / benzene / 1.5 h / Ambient temperature

17: Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

18: Li, NH₃ / tetrahydrofuran / 1.5 h / -78 °C

19: Et₃N / CH₂Cl₂ / 1.25 h / Ambient temperature

20: tetrahydrofuran / 0.5 h / -35 - -10 °C

With 1H-imidazole; hydrogenchloride; potassium cyanide; Oxone; sodium tetrahydroborate; 18-crown-6 ether; potassium tert-butylate; 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) → (4R,5S,7R,8R,9R,10S,12S,14R,16S)-20-(Methanesulfonyl)-16-ethoxy-13-oxo-12-(phenylseleno)-21-norpicras-2-ene (155039-11-5)

Guidance literature:

Multi-step reaction with 19 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

15: 89.6 percent / t-BuOK / benzene / 1.5 h / Ambient temperature

16: Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

17: Li, NH₃ / tetrahydrofuran / 1.5 h / -78 °C

18: Et₃N / CH₂Cl₂ / 1.25 h / Ambient temperature

19: tetrahydrofuran / 0.5 h / -35 - -10 °C

With 1H-imidazole; hydrogenchloride; potassium cyanide; Oxone; sodium tetrahydroborate; 18-crown-6 ether; potassium tert-butylate; 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; In tetrahydrofuran; 1,4-dioxane; diethyl ether; ethanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; benzene;

DOI:10.1021/jo00081a008

Reference yield:

(1R,4aS,4bR,9R,10aS)-9-<(tert-Butyldimethylsilyl)oxy>-1,4,4a,4b,5,6,7,9,10,10a-decahydro-1,4a-dimethylphenanthren-7-one (155028-05-0) → (4R,5S,7R,8R,9R,10S,12S,14R,16S)-20-(Methanesulfonyl)-16-ethoxy-13-oxo-12-(phenylseleno)-21-norpicras-2-ene (155039-11-5)

Guidance literature:

Multi-step reaction with 13 steps

1: 87 percent / KCN, 18-crown-6 ether / benzene; toluene / 24 h / Ambient temperature

2: Et₃N / CH₂Cl₂ / 1.5 h / 0 °C

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

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

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

6: 10percent aq. HCl / 20 h / Ambient temperature

7: 95.5 percent / (n-Bu)4NF / tetrahydrofuran / Ambient temperature

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

9: 89.6 percent / t-BuOK / benzene / 1.5 h / Ambient temperature

10: Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

11: Li, NH₃ / tetrahydrofuran / 1.5 h / -78 °C

12: Et₃N / CH₂Cl₂ / 1.25 h / Ambient temperature

13: tetrahydrofuran / 0.5 h / -35 - -10 °C

With hydrogenchloride; potassium cyanide; 18-crown-6 ether; potassium tert-butylate; tetrabutyl ammonium fluoride; ammonia; bromine; tetra-(n-butyl)ammonium iodide; lithium; sodium hydride; diisobutylaluminium hydride; triethylamine; 2,3-Dimethylaniline; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; toluene; benzene;

DOI:10.1021/jo00081a008

upstream raw materials:

(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

(1R,4aS,4bR,9R,10aS)-9-<(tert-Butyldimethylsilyl)oxy>-1,4,4a,4b,5,6,7,9,10,10a-decahydro-1,4a-dimethylphenanthren-7-one

(1S,2S,4aS,4bR,10aS)-1,2,3,4,4a,4b,5,6,10,10a-decahydro-2-(methanesulfonyl)-7-methoxy-1,4a-dimethylphenanthrene

Downstream raw materials:

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