(1S,3S,5R,3a'R,7a'S)-3-[(tert-butyldiphenylsilyl)oxymethyl]-5,3a',7a'-trimethyl-2-oxaspiro[cyclopentane-1,1'-hexahydroindan]-4'-one

Base Information

• Chemical Name: (1S,3S,5R,3a'R,7a'S)-3-[(tert-butyldiphenylsilyl)oxymethyl]-5,3a',7a'-trimethyl-2-oxaspiro[cyclopentane-1,1'-hexahydroindan]-4'-one
• CAS No.: 1582753-36-3
• Molecular Formula: C₃₂H₄₄O₃Si
• Molecular Weight: 504.785

Synonyms:(1S,3S,5R,3a'R,7a'S)-3-[(tert-butyldiphenylsilyl)oxymethyl]-5,3a',7a'-trimethyl-2-oxaspiro[cyclopentane-1,1'-hexahydroindan]-4'-one

Chemical Property of (1S,3S,5R,3a'R,7a'S)-3-[(tert-butyldiphenylsilyl)oxymethyl]-5,3a',7a'-trimethyl-2-oxaspiro[cyclopentane-1,1'-hexahydroindan]-4'-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,3S,5R,3a'R,7a'S)-3-[(tert-butyldiphenylsilyl)oxymethyl]-5,3a',7a'-trimethyl-2-oxaspiro[cyclopentane-1,1'-hexahydroindan]-4'-one

There total 19 articles about (1S,3S,5R,3a'R,7a'S)-3-[(tert-butyldiphenylsilyl)oxymethyl]-5,3a',7a'-trimethyl-2-oxaspiro[cyclopentane-1,1'-hexahydroindan]-4'-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: 88.0%

(1S,3S,5R,3a'R,4'R,7a'S)-3-[(tert-butyldiphenylsilyl)oxymethyl]-5,3a',7a'-trimethyl-2-oxaspiro-[cyclopentane-1,1'-hexahydroindan]-4'-ol → (1S,3S,5R,3a'R,7a'S)-3-[(tert-butyldiphenylsilyl)oxymethyl]-5,3a',7a'-trimethyl-2-oxaspiro[cyclopentane-1,1'-hexahydroindan]-4'-one (1582753-36-3)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; at 0 - 20 ℃; for 0.5h; Inert atmosphere;

DOI:10.1021/ol500657f

Reference yield:

[2S,2(1S),5S]-[5-(tert-butyldiphenylsilyloxy)methyl-2-(1-methylcyclohex-2-en-1-yl)-3-methylenetetrahydrofuran-2-yl]methanol (1582752-99-5) → (1S,3S,5R,3a'R,7a'S)-3-[(tert-butyldiphenylsilyl)oxymethyl]-5,3a',7a'-trimethyl-2-oxaspiro[cyclopentane-1,1'-hexahydroindan]-4'-one (1582753-36-3)

Guidance literature:

Multi-step reaction with 17 steps

1: Dess-Martin periodane / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere

2: N,N,N',N'-tetramethylguanidine / 10 h / Inert atmosphere

3: sulfuric acid / 2 h / 0 °C

4: triethylamine / dichloromethane / 0.5 h / 20 °C / Inert atmosphere

5: sodium tetrahydroborate; ethanol / 1,4-dioxane / 7 h / 0 - 20 °C / Inert atmosphere

6: phenyl isocyanate; triethylamine / benzene / 6 h / Reflux; Inert atmosphere

7: diisobutylaluminium hydride / hexane; toluene / 0.25 h / -20 °C / Inert atmosphere

8: platinum(IV) oxide; hydrogen / ethyl acetate / 16 h / 760.05 Torr

9: sodium carbonate / acetone / 0.5 h / Inert atmosphere

10: Dess-Martin periodane / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere

11: trifluoroacetic acid / toluene / 8 h / 60 °C

12: sodium tetrahydroborate; cerium(III) chloride heptahydrate / methanol / 0.5 h / -40 °C / Inert atmosphere

13: diethylzinc / dichloromethane / 9 h / 0 °C / Inert atmosphere

14: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 60 °C

15: platinum(IV) oxide; hydrogen; sodium acetate / acetic acid / 48 h / 40 °C / 760.05 Torr

16: 1H-imidazole / N,N-dimethyl-formamide / 6 h / 0 - 20 °C / Inert atmosphere

17: Dess-Martin periodane / dichloromethane / 0.5 h / 0 - 20 °C / Inert atmosphere

With 1H-imidazole; platinum(IV) oxide; sodium tetrahydroborate; ethanol; cerium(III) chloride heptahydrate; sulfuric acid; tetrabutyl ammonium fluoride; hydrogen; diethylzinc; sodium acetate; diisobutylaluminium hydride; sodium carbonate; Dess-Martin periodane; phenyl isocyanate; triethylamine; trifluoroacetic acid; N,N,N',N'-tetramethylguanidine; In tetrahydrofuran; 1,4-dioxane; methanol; hexane; dichloromethane; acetic acid; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene; benzene; 1: |Dess-Martin Oxidation / 10: |Dess-Martin Oxidation;

DOI:10.1021/ol500657f

Reference yield:

[2S,2(1S),5S]-5-[(tert-butyldiphenylsilyl)oxymethyl]-2-(1-methylcyclohex-2-en-1-yl)-3-methylenetetrahydrofuran-2-carbaldehyde (1582753-01-2) → (1S,3S,5R,3a'R,7a'S)-3-[(tert-butyldiphenylsilyl)oxymethyl]-5,3a',7a'-trimethyl-2-oxaspiro[cyclopentane-1,1'-hexahydroindan]-4'-one (1582753-36-3)

Guidance literature:

Multi-step reaction with 16 steps

1: N,N,N',N'-tetramethylguanidine / 10 h / Inert atmosphere

2: sulfuric acid / 2 h / 0 °C

3: triethylamine / dichloromethane / 0.5 h / 20 °C / Inert atmosphere

4: sodium tetrahydroborate; ethanol / 1,4-dioxane / 7 h / 0 - 20 °C / Inert atmosphere

5: phenyl isocyanate; triethylamine / benzene / 6 h / Reflux; Inert atmosphere

6: diisobutylaluminium hydride / hexane; toluene / 0.25 h / -20 °C / Inert atmosphere

7: platinum(IV) oxide; hydrogen / ethyl acetate / 16 h / 760.05 Torr

8: sodium carbonate / acetone / 0.5 h / Inert atmosphere

9: Dess-Martin periodane / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere

10: trifluoroacetic acid / toluene / 8 h / 60 °C

11: sodium tetrahydroborate; cerium(III) chloride heptahydrate / methanol / 0.5 h / -40 °C / Inert atmosphere

12: diethylzinc / dichloromethane / 9 h / 0 °C / Inert atmosphere

13: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 60 °C

14: platinum(IV) oxide; hydrogen; sodium acetate / acetic acid / 48 h / 40 °C / 760.05 Torr

15: 1H-imidazole / N,N-dimethyl-formamide / 6 h / 0 - 20 °C / Inert atmosphere

16: Dess-Martin periodane / dichloromethane / 0.5 h / 0 - 20 °C / Inert atmosphere

With 1H-imidazole; platinum(IV) oxide; sodium tetrahydroborate; ethanol; cerium(III) chloride heptahydrate; sulfuric acid; tetrabutyl ammonium fluoride; hydrogen; diethylzinc; sodium acetate; diisobutylaluminium hydride; sodium carbonate; Dess-Martin periodane; phenyl isocyanate; triethylamine; trifluoroacetic acid; N,N,N',N'-tetramethylguanidine; In tetrahydrofuran; 1,4-dioxane; methanol; hexane; dichloromethane; acetic acid; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene; benzene; 9: |Dess-Martin Oxidation;

DOI:10.1021/ol500657f

upstream raw materials:

C₃₀H₃₈O₄Si

methyl [2S,2(1S),5S]-5-[(tert-butyldiphenylsilyl)oxymethyl]-2-(1-methylcyclohex-2-en-1-yl)-3-methylenetetrahydrofuran-2-carboxylate

[2S,2(1S),5S]-[5-(tert-butyldiphenylsilyloxy)methyl-2-(1-methylcyclohex-2-en-1-yl)-3-methylenetetrahydrofuran-2-yl]methanol

[2S,2(1S),5S]-5-[(tert-butyldiphenylsilyl)oxymethyl]-2-(1-methylcyclohex-2-en-1-yl)-3-methylenetetrahydrofuran-2-carbaldehyde

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