[(4S,6S,6aR,9S)-2-Benzyloxy-4-(tert-butyl-diphenyl-silanyloxymethyl)-3,6,9-trimethyl-5,6,6a,7,8,9-hexahydro-4H-phenalen-1-yl]-methanol

Base Information

• Chemical Name: [(4S,6S,6aR,9S)-2-Benzyloxy-4-(tert-butyl-diphenyl-silanyloxymethyl)-3,6,9-trimethyl-5,6,6a,7,8,9-hexahydro-4H-phenalen-1-yl]-methanol
• CAS No.: 113180-37-3
• Molecular Formula: C₄₁H₅₀O₃Si
• Molecular Weight: 618.932

Synonyms:

Chemical Property of [(4S,6S,6aR,9S)-2-Benzyloxy-4-(tert-butyl-diphenyl-silanyloxymethyl)-3,6,9-trimethyl-5,6,6a,7,8,9-hexahydro-4H-phenalen-1-yl]-methanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(4S,6S,6aR,9S)-2-Benzyloxy-4-(tert-butyl-diphenyl-silanyloxymethyl)-3,6,9-trimethyl-5,6,6a,7,8,9-hexahydro-4H-phenalen-1-yl]-methanol

There total 21 articles about [(4S,6S,6aR,9S)-2-Benzyloxy-4-(tert-butyl-diphenyl-silanyloxymethyl)-3,6,9-trimethyl-5,6,6a,7,8,9-hexahydro-4H-phenalen-1-yl]-methanol 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:

(6S,6aR,9S)-2-Benzyloxy-4-(tert-butyl-diphenyl-silanyloxymethyl)-3,6,9-trimethyl-5,6,6a,7,8,9-hexahydro-4H-phenalene-1-carboxylic acid methyl ester → [(4R,6S,6aR,9S)-2-Benzyloxy-4-(tert-butyl-diphenyl-silanyloxymethyl)-3,6,9-trimethyl-5,6,6a,7,8,9-hexahydro-4H-phenalen-1-yl]-methanol (113299-29-9) + [(4S,6S,6aR,9S)-2-Benzyloxy-4-(tert-butyl-diphenyl-silanyloxymethyl)-3,6,9-trimethyl-5,6,6a,7,8,9-hexahydro-4H-phenalen-1-yl]-methanol (113180-37-3)

Guidance literature:

With diisopropyl aluminum hydride; In dichloromethane; at 20 ℃; Yield given. Yields of byproduct given;

DOI:10.1021/jo00242a053

Reference yield:

(1S,2S,5S)-5-(1-hydroxypropan-2-yl)-2-methylcyclohexanol → [(4S,6S,6aR,9S)-2-Benzyloxy-4-(tert-butyl-diphenyl-silanyloxymethyl)-3,6,9-trimethyl-5,6,6a,7,8,9-hexahydro-4H-phenalen-1-yl]-methanol (113180-37-3)

Guidance literature:

Multi-step reaction with 22 steps

1: pyridine

2: pyridinium p-toluenesulfonate (PPTS) / CH₂Cl₂

3: aq. KOH

4: pyridinium chlorochromate (PCC) , NaOAc / CH₂Cl₂

5: NaClO₂, 2-methyl-2-butene / 2-methyl-propan-2-ol; H₂O

6: aq. acetic acid / 80 °C

7: 67 percent / p-toluenesulfonic acid / toluene / Heating

8: lithium diisopropylamide (LDA) / hexamethylphosphoric acid triamide

9: H₂O₂

10: 79 percent / CuI, dimethyl sulfide, trimethylsilyl chloride / tetrahydrofuran / -40 °C

11: 84 percent / LiAlH₄ / tetrahydrofuran / 1 h / 25 °C

12: Et₃N, 4-(dimethylamino)pyridine (DMAP) / CH₂Cl₂

13: lithium triethylborohydride / tetrahydrofuran

14: pyridinium chlorochromate (PCC) / CH₂Cl₂

15: NaH / dioxane

16: Et₃N / hexane

17: 1.) TiCl₄, 2.) NaOMe / 1.) CH₂Cl₂, -78 deg C, 4 h, 2.) MeOH, 24 h

18: m-chloroperbenzoic acid (MCPBA), NaHCO₃ / CHCl₃ / 55 °C

19: SnCl₄ / CH₂Cl₂ / 20 °C

20: K₂CO₃ / dimethylsulfoxide

21: imidazole / dimethylformamide / 45 °C

22: diisopropylaluminum hydride (DIBAL) / CH₂Cl₂ / 20 °C

With pyridine; 1H-imidazole; dmap; potassium hydroxide; sodium chlorite; copper(l) iodide; lithium aluminium tetrahydride; chloro-trimethyl-silane; 2-methyl-but-2-ene; diisopropyl aluminum hydride; dimethylsulfide; dihydrogen peroxide; sodium methylate; sodium acetate; pyridinium p-toluenesulfonate; titanium tetrachloride; tin(IV) chloride; sodium hydride; lithium triethylborohydride; sodium hydrogencarbonate; potassium carbonate; toluene-4-sulfonic acid; acetic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; lithium diisopropyl amide; In tetrahydrofuran; 1,4-dioxane; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; dichloromethane; chloroform; water; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; tert-butyl alcohol;

DOI:10.1021/jo00242a053

Reference yield:

(1S,5S,8S)-4,8-Dimethyl-2-oxa-bicyclo[3.3.1]nonan-3-one → [(4S,6S,6aR,9S)-2-Benzyloxy-4-(tert-butyl-diphenyl-silanyloxymethyl)-3,6,9-trimethyl-5,6,6a,7,8,9-hexahydro-4H-phenalen-1-yl]-methanol (113180-37-3)

Guidance literature:

Multi-step reaction with 15 steps

1: lithium diisopropylamide (LDA) / hexamethylphosphoric acid triamide

2: H₂O₂

3: 79 percent / CuI, dimethyl sulfide, trimethylsilyl chloride / tetrahydrofuran / -40 °C

4: 84 percent / LiAlH₄ / tetrahydrofuran / 1 h / 25 °C

5: Et₃N, 4-(dimethylamino)pyridine (DMAP) / CH₂Cl₂

6: lithium triethylborohydride / tetrahydrofuran

7: pyridinium chlorochromate (PCC) / CH₂Cl₂

8: NaH / dioxane

9: Et₃N / hexane

10: 1.) TiCl₄, 2.) NaOMe / 1.) CH₂Cl₂, -78 deg C, 4 h, 2.) MeOH, 24 h

11: m-chloroperbenzoic acid (MCPBA), NaHCO₃ / CHCl₃ / 55 °C

12: SnCl₄ / CH₂Cl₂ / 20 °C

13: K₂CO₃ / dimethylsulfoxide

14: imidazole / dimethylformamide / 45 °C

15: diisopropylaluminum hydride (DIBAL) / CH₂Cl₂ / 20 °C

With 1H-imidazole; dmap; copper(l) iodide; lithium aluminium tetrahydride; chloro-trimethyl-silane; diisopropyl aluminum hydride; dimethylsulfide; dihydrogen peroxide; sodium methylate; titanium tetrachloride; tin(IV) chloride; sodium hydride; lithium triethylborohydride; sodium hydrogencarbonate; potassium carbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; lithium diisopropyl amide; In tetrahydrofuran; 1,4-dioxane; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; dichloromethane; chloroform; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1021/jo00242a053

upstream raw materials:

(2S,5S)-2-Methyl-5-((S)-1-methyl-but-3-enyl)-cyclohexanone

(1S,5S,8S)-8-Methyl-4-methylene-2-oxa-bicyclo[3.3.1]nonan-3-one

(1S,2S,5S)-5-((S)-1-Hydroxymethyl-but-3-enyl)-2-methyl-cyclohexanol

(1S,4S,5S,8S)-4-Allyl-8-methyl-2-oxa-bicyclo[3.3.1]nonan-3-one

Downstream raw materials:

Acetic acid (2S,3R,4S,5R)-4,5-diacetoxy-2-[(4R,6S,6aR,9S)-2-benzyloxy-3,6,9-trimethyl-4-(2-methyl-propenyl)-5,6,6a,7,8,9-hexahydro-4H-phenalen-1-yloxy]-tetrahydro-pyran-3-yl ester

Formic acid (4S,6S,6aR,9S)-2-benzyloxy-4-(tert-butyl-diphenyl-silanyloxymethyl)-3,6,9-trimethyl-5,6,6a,7,8,9-hexahydro-4H-phenalen-1-yl ester

(2S,3R,4S,5R)-2-[(4R,6S,6aR,9S)-2-Benzyloxy-3,6,9-trimethyl-4-(2-methyl-propenyl)-5,6,6a,7,8,9-hexahydro-4H-phenalen-1-yloxy]-tetrahydro-pyran-3,4,5-triol

Formic acid (4S,6S,6aR,9S)-2-benzyloxy-4-formyl-3,6,9-trimethyl-5,6,6a,7,8,9-hexahydro-4H-phenalen-1-yl ester

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