(1R,4aS,4bR,8aS,9R,10aS)-8a-Benzyloxymethyl-7,9-bis-(tert-butyl-dimethyl-silanyloxy)-1,4a-dimethyl-1,4,4a,4b,5,8,8a,9,10,10a-decahydro-phenanthrene

Base Information

• Chemical Name: (1R,4aS,4bR,8aS,9R,10aS)-8a-Benzyloxymethyl-7,9-bis-(tert-butyl-dimethyl-silanyloxy)-1,4a-dimethyl-1,4,4a,4b,5,8,8a,9,10,10a-decahydro-phenanthrene
• CAS No.: 155028-09-4
• Molecular Formula: C₃₆H₆₀O₃Si₂
• Molecular Weight: 597.042
• Mol file: 155028-09-4.mol

Synonyms:

Chemical Property of (1R,4aS,4bR,8aS,9R,10aS)-8a-Benzyloxymethyl-7,9-bis-(tert-butyl-dimethyl-silanyloxy)-1,4a-dimethyl-1,4,4a,4b,5,8,8a,9,10,10a-decahydro-phenanthrene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,4aS,4bR,8aS,9R,10aS)-8a-Benzyloxymethyl-7,9-bis-(tert-butyl-dimethyl-silanyloxy)-1,4a-dimethyl-1,4,4a,4b,5,8,8a,9,10,10a-decahydro-phenanthrene

There total 12 articles about (1R,4aS,4bR,8aS,9R,10aS)-8a-Benzyloxymethyl-7,9-bis-(tert-butyl-dimethyl-silanyloxy)-1,4a-dimethyl-1,4,4a,4b,5,8,8a,9,10,10a-decahydro-phenanthrene 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-Benzyloxymethyl-7,9-bis-(tert-butyl-dimethyl-silanyloxy)-1,4a-dimethyl-1,4,4a,4b,5,8,8a,9,10,10a-decahydro-phenanthrene (155028-09-4)

Guidance literature:

Multi-step reaction with 12 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

With 1H-imidazole; potassium cyanide; Oxone; sodium tetrahydroborate; 18-crown-6 ether; ammonia; dihydrogen peroxide; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; lithium; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; triethylamine; 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-Benzyloxymethyl-7,9-bis-(tert-butyl-dimethyl-silanyloxy)-1,4a-dimethyl-1,4,4a,4b,5,8,8a,9,10,10a-decahydro-phenanthrene (155028-09-4)

Guidance literature:

Multi-step reaction with 11 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

With 1H-imidazole; potassium cyanide; Oxone; sodium tetrahydroborate; 18-crown-6 ether; dihydrogen peroxide; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; triethylamine; 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) → (1R,4aS,4bR,8aS,9R,10aS)-8a-Benzyloxymethyl-7,9-bis-(tert-butyl-dimethyl-silanyloxy)-1,4a-dimethyl-1,4,4a,4b,5,8,8a,9,10,10a-decahydro-phenanthrene (155028-09-4)

Guidance literature:

Multi-step reaction with 5 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

With potassium cyanide; 18-crown-6 ether; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; triethylamine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; toluene; benzene;

DOI:10.1021/jo00081a008

upstream raw materials:

benzyl bromide

(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

Downstream raw materials:

(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

(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