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

Base Information

Chemical Name:4-<(tert-butyldiphenylsilyl)oxy>-9-<(2-methoxyethoxy)methoxy>-6-methylene-3aα,4β,5,6,6α,7,8,9α,9aα,9bα-decahydroazuleno<4,5-b>furan-2(3H)-one
CAS No.:105620-13-1
Molecular Formula:C₃₃H₄₄O₆Si
Molecular Weight:564.794
Hs Code.:

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

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

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

There total 25 articles about 4-<(tert-butyldiphenylsilyl)oxy>-9-<(2-methoxyethoxy)methoxy>-6-methylene-3aα,4β,5,6,6α,7,8,9α,9aα,9bα-decahydroazuleno<4,5-b>furan-2(3H)-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: 99.0%

: 105620-00-6
4-hydroxy-9-<(2-methoxyethoxy)methoxy>-6-methylene-3aα,4β,5,6,6α,7,8,9α,9aα,9bα-decahydroazuleno<4.5-b>furan-2(3H)-one

: 58479-61-1
tert-butylchlorodiphenylsilane

: 105620-13-1
4-<(tert-butyldiphenylsilyl)oxy>-9-<(2-methoxyethoxy)methoxy>-6-methylene-3aα,4β,5,6,6α,7,8,9α,9aα,9bα-decahydroazuleno<4,5-b>furan-2(3H)-one

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; for 22h; Ambient temperature;
DOI:10.1021/jo00377a006

Reference yield:

: 93111-81-0
2-<2-(1,3-dioxolan-2-yl)ethyl>-3,5-cycloheptadien-1-ol

: 105620-13-1
4-<(tert-butyldiphenylsilyl)oxy>-9-<(2-methoxyethoxy)methoxy>-6-methylene-3aα,4β,5,6,6α,7,8,9α,9aα,9bα-decahydroazuleno<4,5-b>furan-2(3H)-one

Guidance literature:: Multi-step reaction with 15 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

With pyridine; 1H-imidazole; chromium(VI) oxide; methanol; tert.-butylhydroperoxide; dmap; bis(acetylacetonate)oxovanadium; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; potassium carbonate; triethylamine; diisopropylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; zinc; lithium diisopropyl amide; phosphorous acid trimethyl ester; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetone;
DOI:10.1021/jo00377a006

Reference yield:

: 106900-10-1
1-acetoxy-2-<2-(1,3-dioxolan-2-yl)ethyl>-3,5-cycloheptadiene

: 105620-13-1
4-<(tert-butyldiphenylsilyl)oxy>-9-<(2-methoxyethoxy)methoxy>-6-methylene-3aα,4β,5,6,6α,7,8,9α,9aα,9bα-decahydroazuleno<4,5-b>furan-2(3H)-one

Guidance literature:: Multi-step reaction with 14 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

With pyridine; 1H-imidazole; chromium(VI) oxide; methanol; tert.-butylhydroperoxide; bis(acetylacetonate)oxovanadium; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; potassium carbonate; diisopropylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; zinc; lithium diisopropyl amide; phosphorous acid trimethyl ester; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetone;
DOI:10.1021/jo00377a006