rel-(1S,3aR,7aS)-Methyl 1-<2-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-1(S)-methylethyl>-1,2,3,4,5,6,7,7a-octahydro-4(E)-<(2,5-dimethoxyphenyl)methylene>-3aH-indene-1-carboxylate

Base Information

Chemical Name:rel-(1S,3aR,7aS)-Methyl 1-<2-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-1(S)-methylethyl>-1,2,3,4,5,6,7,7a-octahydro-4(E)-<(2,5-dimethoxyphenyl)methylene>-3aH-indene-1-carboxylate
CAS No.:112946-35-7
Molecular Formula:C₂₉H₄₆O₅Si
Molecular Weight:502.767
Hs Code.:

rel-(1S,3aR,7aS)-Methyl 1-<2-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-1(S)-methylethyl>-1,2,3,4,5,6,7,7a-octahydro-4(E)-<(2,5-dimethoxyphenyl)methylene>-3aH-indene-1-carboxylate

Synonyms:rel-(1S,3aR,7aS)-Methyl 1-<2-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-1(S)-methylethyl>-1,2,3,4,5,6,7,7a-octahydro-4(E)-<(2,5-dimethoxyphenyl)methylene>-3aH-indene-1-carboxylate

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Chemical Property of rel-(1S,3aR,7aS)-Methyl 1-<2-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-1(S)-methylethyl>-1,2,3,4,5,6,7,7a-octahydro-4(E)-<(2,5-dimethoxyphenyl)methylene>-3aH-indene-1-carboxylate

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Technology Process of rel-(1S,3aR,7aS)-Methyl 1-<2-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-1(S)-methylethyl>-1,2,3,4,5,6,7,7a-octahydro-4(E)-<(2,5-dimethoxyphenyl)methylene>-3aH-indene-1-carboxylate

There total 14 articles about rel-(1S,3aR,7aS)-Methyl 1-<2-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-1(S)-methylethyl>-1,2,3,4,5,6,7,7a-octahydro-4(E)-<(2,5-dimethoxyphenyl)methylene>-3aH-indene-1-carboxylate 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:

: 99474-48-3,99529-34-7,122923-96-0,122999-24-0
rel-<1R(E),5R,8R>-Ethyl 5-(8-iodo-7-oxo-6-oxabicyclo<3.2.1>oct-2-en-1-yl)-2-methyl-2-pentenoate

: 112946-35-7
rel-(1S,3aR,7aS)-Methyl 1-<2-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-1(S)-methylethyl>-1,2,3,4,5,6,7,7a-octahydro-4(E)-<(2,5-dimethoxyphenyl)methylene>-3aH-indene-1-carboxylate

Guidance literature:: Multi-step reaction with 10 steps

1: n-Bu₃SnH / AIBN / benzene / 3.5 h / 60 °C

2: 95 percent / LiAlH₄ / tetrahydrofuran / 1 h

3: 98 percent / imidazole / dimethylformamide / 18.5 h / 35 °C

4: 87 percent / MCPBA / CH₂Cl₂ / 68 h / Ambient temperature

5: 69 percent / LiNEt₂ / diethyl ether; hexane / 0.25 h / Ambient temperature

6: 67 percent / EtNH₂, Li / 1.5 h

7: CH₂Cl₂

8: 1.) (COCl₂)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, 1 h, 2.) 65 min

9: 1.) CeCl₃ / 1.) THF, 35 min, 2.) 2 h

10: SOCl₂, pyridine / 1 h

With pyridine; 1H-imidazole; lithium aluminium tetrahydride; thionyl chloride; cerium(III) chloride; (COCl₂)2; lithium diethylamide; tri-n-butyl-tin hydride; lithium; ethylamine; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; 2,2'-azobis(isobutyronitrile); In tetrahydrofuran; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; benzene;
DOI:10.1021/ja00201a035

Reference yield:

: 85585-60-0,114837-68-2
rel-(1S,5S,8R)-8-iodo-1-(3-oxopropyl)-6-oxabicyclo<3.2.1>oct-2-en-7-one

: 112946-35-7
rel-(1S,3aR,7aS)-Methyl 1-<2-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-1(S)-methylethyl>-1,2,3,4,5,6,7,7a-octahydro-4(E)-<(2,5-dimethoxyphenyl)methylene>-3aH-indene-1-carboxylate

Guidance literature:: Multi-step reaction with 11 steps

1: 94.4 percent / benzene / 4.5 h / 75 °C

2: n-Bu₃SnH / AIBN / benzene / 3.5 h / 60 °C

3: 95 percent / LiAlH₄ / tetrahydrofuran / 1 h

4: 98 percent / imidazole / dimethylformamide / 18.5 h / 35 °C

5: 87 percent / MCPBA / CH₂Cl₂ / 68 h / Ambient temperature

6: 69 percent / LiNEt₂ / diethyl ether; hexane / 0.25 h / Ambient temperature

7: 67 percent / EtNH₂, Li / 1.5 h

8: CH₂Cl₂

9: 1.) (COCl₂)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, 1 h, 2.) 65 min

10: 1.) CeCl₃ / 1.) THF, 35 min, 2.) 2 h

11: SOCl₂, pyridine / 1 h

With pyridine; 1H-imidazole; lithium aluminium tetrahydride; thionyl chloride; cerium(III) chloride; (COCl₂)2; lithium diethylamide; tri-n-butyl-tin hydride; lithium; ethylamine; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; 2,2'-azobis(isobutyronitrile); In tetrahydrofuran; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; benzene;
DOI:10.1021/ja00201a035

Reference yield:

: 99474-53-0,122999-30-8
rel-(1R,3aS,7R,7aS)-1-<2-Hydroxy-1(S)-methylethyl>-1,2,3,6,7,7a-hexahydro-7,3a-(epoxymethano)-3aH-inden-9-one

: 112946-35-7
rel-(1S,3aR,7aS)-Methyl 1-<2-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-1(S)-methylethyl>-1,2,3,4,5,6,7,7a-octahydro-4(E)-<(2,5-dimethoxyphenyl)methylene>-3aH-indene-1-carboxylate

Guidance literature:: Multi-step reaction with 8 steps

1: 98 percent / imidazole / dimethylformamide / 18.5 h / 35 °C

2: 87 percent / MCPBA / CH₂Cl₂ / 68 h / Ambient temperature

3: 69 percent / LiNEt₂ / diethyl ether; hexane / 0.25 h / Ambient temperature

4: 67 percent / EtNH₂, Li / 1.5 h

5: CH₂Cl₂

6: 1.) (COCl₂)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, 1 h, 2.) 65 min

7: 1.) CeCl₃ / 1.) THF, 35 min, 2.) 2 h

8: SOCl₂, pyridine / 1 h

With pyridine; 1H-imidazole; thionyl chloride; cerium(III) chloride; (COCl₂)2; lithium diethylamide; lithium; ethylamine; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; In diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja00201a035