(3S,5S)-5-[[3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-methoxyphenyl]methyl]-3-ethenyl-1-cyclopentene-1-carboxylic acid methyl ester

Base Information

Chemical Name:(3S,5S)-5-[[3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-methoxyphenyl]methyl]-3-ethenyl-1-cyclopentene-1-carboxylic acid methyl ester
CAS No.:944282-77-3
Molecular Formula:C₂₃H₃₄O₄Si
Molecular Weight:402.606
Hs Code.:

Synonyms:(3S,5S)-5-[[3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-methoxyphenyl]methyl]-3-ethenyl-1-cyclopentene-1-carboxylic acid methyl ester

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Chemical Property of (3S,5S)-5-[[3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-methoxyphenyl]methyl]-3-ethenyl-1-cyclopentene-1-carboxylic acid methyl ester

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Technology Process of (3S,5S)-5-[[3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-methoxyphenyl]methyl]-3-ethenyl-1-cyclopentene-1-carboxylic acid methyl ester

There total 5 articles about (3S,5S)-5-[[3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-methoxyphenyl]methyl]-3-ethenyl-1-cyclopentene-1-carboxylic acid methyl ester 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:

: C₂₆H₄₂O₅Si

: 944282-77-3
(3S,5S)-5-[[3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-methoxyphenyl]methyl]-3-ethenyl-1-cyclopentene-1-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

2.1: 82 percent / SmI₂ / methanol; tetrahydrofuran / 5 h / 0 °C

3.1: potassium 1,1,1,3,3,3-hexamethyldisilazide / tetrahydrofuran / 1 h / -78 °C

3.2: 92 percent / tetrahydrofuran / 2 h

4.1: 77 percent / Ph₃P; Et₃N / Pd(OAc)2 / dimethylformamide / 24 h

With samarium diiodide; Dess-Martin periodane; triethylamine; triphenylphosphine; palladium diacetate; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1002/anie.200700517

Reference yield:

: 944282-72-8
(1S,3S,5R,6S)-3-[[3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-methoxyphenyl]methyl]-2-oxobicyclo[3.1.0]hexane-6-carboxylic acid ethyl ester

: 944282-77-3
(3S,5S)-5-[[3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-methoxyphenyl]methyl]-3-ethenyl-1-cyclopentene-1-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: LiAlH₄ / tetrahydrofuran / 4 h / 0 - 20 °C

2.1: pyridine / tetrahydrofuran / 1.5 h / 0 - 20 °C

3.1: Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

4.1: 82 percent / SmI₂ / methanol; tetrahydrofuran / 5 h / 0 °C

5.1: potassium 1,1,1,3,3,3-hexamethyldisilazide / tetrahydrofuran / 1 h / -78 °C

5.2: 92 percent / tetrahydrofuran / 2 h

6.1: 77 percent / Ph₃P; Et₃N / Pd(OAc)2 / dimethylformamide / 24 h

With pyridine; lithium aluminium tetrahydride; samarium diiodide; Dess-Martin periodane; triethylamine; triphenylphosphine; palladium diacetate; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1002/anie.200700517

Reference yield:

: 944282-73-9
C₂₁H₃₄O₄Si

: 944282-77-3
(3S,5S)-5-[[3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-methoxyphenyl]methyl]-3-ethenyl-1-cyclopentene-1-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: pyridine / tetrahydrofuran / 1.5 h / 0 - 20 °C

2.1: Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

3.1: 82 percent / SmI₂ / methanol; tetrahydrofuran / 5 h / 0 °C

4.1: potassium 1,1,1,3,3,3-hexamethyldisilazide / tetrahydrofuran / 1 h / -78 °C

4.2: 92 percent / tetrahydrofuran / 2 h

5.1: 77 percent / Ph₃P; Et₃N / Pd(OAc)2 / dimethylformamide / 24 h

With pyridine; samarium diiodide; Dess-Martin periodane; triethylamine; triphenylphosphine; palladium diacetate; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1002/anie.200700517