4-<(terrt-butyldiphenylsilyl)oxy>-6-methylene-3aα,4,5,6,6aα,7,8,9β-octahydroazuleno<4,5-b>furan-2-(3H),9(9aαH)-dione

Base Information

• Chemical Name: 4-<(terrt-butyldiphenylsilyl)oxy>-6-methylene-3aα,4,5,6,6aα,7,8,9β-octahydroazuleno<4,5-b>furan-2-(3H),9(9aαH)-dione
• CAS No.: 105638-41-3
• Molecular Formula: C₂₉H₃₄O₄Si
• Molecular Weight: 474.672

Synonyms:

Chemical Property of 4-<(terrt-butyldiphenylsilyl)oxy>-6-methylene-3aα,4,5,6,6aα,7,8,9β-octahydroazuleno<4,5-b>furan-2-(3H),9(9aαH)-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-<(terrt-butyldiphenylsilyl)oxy>-6-methylene-3aα,4,5,6,6aα,7,8,9β-octahydroazuleno<4,5-b>furan-2-(3H),9(9aαH)-dione

There total 27 articles about 4-<(terrt-butyldiphenylsilyl)oxy>-6-methylene-3aα,4,5,6,6aα,7,8,9β-octahydroazuleno<4,5-b>furan-2-(3H),9(9aαH)-dione 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:

2-<2-(1,3-dioxolan-2-yl)ethyl>-3,5-cycloheptadien-1-ol (93111-81-0) → 4-<(terrt-butyldiphenylsilyl)oxy>-6-methylene-3aα,4,5,6,6aα,7,8,9β-octahydroazuleno<4,5-b>furan-2-(3H),9(9aαH)-dione (105638-41-3)

Guidance literature:

Multi-step reaction with 17 steps

1: 99 percent / Et₃N, 4-(N,N-dimethylamino)pyridine / CH₂Cl₂ / 1.) 0deg C, 30 min, 2.) RT, 30 min

2: 90 percent / 5percent aq. trifluoroacetic acid / acetone / 120 h / Ambient temperature

3: 11.5 g / BF₃*Et₂O / CH₂Cl₂ / 0.08 h / 0 °C

4: 3.4 g / BF₃*Et₂O / 8 h / Ambient temperature

5: 97 percent / diisopropylamine / CH₂Cl₂ / 12 h / Ambient temperature

6: m-chloroperoxybenzoic acid / CH₂Cl₂ / -40 °C

7: trimethylphosphite, methanol / 16 h / 55 °C

8: 96 percent / imidazole / dimethylformamide / 1.5 h / Ambient temperature

9: 86 percent / K₂CO₃ / methanol / 16 h / Ambient temperature

10: 91 percent / CrO₃, pyridine / CH₂Cl₂ / 5 h

11: 1.) Zn / 1.) THF, 0 deg C, 3 d, 2.) THF, CH₂Cl₂

12: 99 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 1 h

13: 65 percent / VO(acac)2, tert-butyl hydroperoxide / CH₂Cl₂ / 1 h / Ambient temperature

14: 1.) lithiumdiisopropyl amide / 1.) DME, hexane, a) from -40 deg C to 60 deg C, b) 60 deg C, 2 h, 2.) DME, hexane, 2.5 h

15: 99 percent / imidazole / dimethylformamide / 22 h / Ambient temperature

16: 96 percent / NaI, trimethylsilyl chloride / acetonitrile / 1 h / -20 °C

17: pyridinium dichromatr (PDC) / CH₂Cl₂ / 48 h / Ambient temperature

With pyridine; 1H-imidazole; chromium(VI) oxide; methanol; tert.-butylhydroperoxide; dmap; dipyridinium dichromate; chloro-trimethyl-silane; bis(acetylacetonate)oxovanadium; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; potassium carbonate; triethylamine; diisopropylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; sodium iodide; zinc; lithium diisopropyl amide; phosphorous acid trimethyl ester; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetone; acetonitrile;

DOI:10.1021/jo00377a006

Reference yield:

1-acetoxy-2-<2-(1,3-dioxolan-2-yl)ethyl>-3,5-cycloheptadiene (106900-10-1) → 4-<(terrt-butyldiphenylsilyl)oxy>-6-methylene-3aα,4,5,6,6aα,7,8,9β-octahydroazuleno<4,5-b>furan-2-(3H),9(9aαH)-dione (105638-41-3)

Guidance literature:

Multi-step reaction with 16 steps

1: 90 percent / 5percent aq. trifluoroacetic acid / acetone / 120 h / Ambient temperature

2: 11.5 g / BF₃*Et₂O / CH₂Cl₂ / 0.08 h / 0 °C

3: 3.4 g / BF₃*Et₂O / 8 h / Ambient temperature

4: 97 percent / diisopropylamine / CH₂Cl₂ / 12 h / Ambient temperature

5: m-chloroperoxybenzoic acid / CH₂Cl₂ / -40 °C

6: trimethylphosphite, methanol / 16 h / 55 °C

7: 96 percent / imidazole / dimethylformamide / 1.5 h / Ambient temperature

8: 86 percent / K₂CO₃ / methanol / 16 h / Ambient temperature

9: 91 percent / CrO₃, pyridine / CH₂Cl₂ / 5 h

10: 1.) Zn / 1.) THF, 0 deg C, 3 d, 2.) THF, CH₂Cl₂

11: 99 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 1 h

12: 65 percent / VO(acac)2, tert-butyl hydroperoxide / CH₂Cl₂ / 1 h / Ambient temperature

13: 1.) lithiumdiisopropyl amide / 1.) DME, hexane, a) from -40 deg C to 60 deg C, b) 60 deg C, 2 h, 2.) DME, hexane, 2.5 h

14: 99 percent / imidazole / dimethylformamide / 22 h / Ambient temperature

15: 96 percent / NaI, trimethylsilyl chloride / acetonitrile / 1 h / -20 °C

16: pyridinium dichromatr (PDC) / CH₂Cl₂ / 48 h / Ambient temperature

With pyridine; 1H-imidazole; chromium(VI) oxide; methanol; tert.-butylhydroperoxide; dipyridinium dichromate; chloro-trimethyl-silane; bis(acetylacetonate)oxovanadium; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; potassium carbonate; diisopropylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; sodium iodide; zinc; lithium diisopropyl amide; phosphorous acid trimethyl ester; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetone; acetonitrile;

DOI:10.1021/jo00377a006

Reference yield:

Acetic acid (1S,3R,4S,7R,8S)-(11-oxa-tricyclo[5.3.1.04,8]undec-9-en-3-yl) ester (105619-83-8,105662-76-8) → 4-<(terrt-butyldiphenylsilyl)oxy>-6-methylene-3aα,4,5,6,6aα,7,8,9β-octahydroazuleno<4,5-b>furan-2-(3H),9(9aαH)-dione (105638-41-3)

Guidance literature:

Multi-step reaction with 14 steps

1: 3.4 g / BF₃*Et₂O / 8 h / Ambient temperature

2: 97 percent / diisopropylamine / CH₂Cl₂ / 12 h / Ambient temperature

3: m-chloroperoxybenzoic acid / CH₂Cl₂ / -40 °C

4: trimethylphosphite, methanol / 16 h / 55 °C

5: 96 percent / imidazole / dimethylformamide / 1.5 h / Ambient temperature

6: 86 percent / K₂CO₃ / methanol / 16 h / Ambient temperature

7: 91 percent / CrO₃, pyridine / CH₂Cl₂ / 5 h

8: 1.) Zn / 1.) THF, 0 deg C, 3 d, 2.) THF, CH₂Cl₂

9: 99 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 1 h

10: 65 percent / VO(acac)2, tert-butyl hydroperoxide / CH₂Cl₂ / 1 h / Ambient temperature

11: 1.) lithiumdiisopropyl amide / 1.) DME, hexane, a) from -40 deg C to 60 deg C, b) 60 deg C, 2 h, 2.) DME, hexane, 2.5 h

12: 99 percent / imidazole / dimethylformamide / 22 h / Ambient temperature

13: 96 percent / NaI, trimethylsilyl chloride / acetonitrile / 1 h / -20 °C

14: pyridinium dichromatr (PDC) / CH₂Cl₂ / 48 h / Ambient temperature

With pyridine; 1H-imidazole; chromium(VI) oxide; methanol; tert.-butylhydroperoxide; dipyridinium dichromate; chloro-trimethyl-silane; bis(acetylacetonate)oxovanadium; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; potassium carbonate; diisopropylamine; 3-chloro-benzenecarboperoxoic acid; sodium iodide; zinc; lithium diisopropyl amide; phosphorous acid trimethyl ester; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jo00377a006

upstream raw materials:

4-<(tert-butyldiphenylsilyl)oxy>-9-hydroxy-6-methylene-3aα,4β,5,6,6α,7,8,9α,9aα,9bα-decahydroazuleno<4,5-b>furan-2(3H)-one

2-<2-(1,3-dioxolan-2-yl)ethyl>-3,5-cycloheptadien-1-ol

1-acetoxy-2-<2-(1,3-dioxolan-2-yl)ethyl>-3,5-cycloheptadiene

1-<(2-methoxyethoxy)methoxy>-4-methylene-1α,2,3,3aα,4,5,6β,8aα-octahydroazulene-6-ol

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