(-)-2-[(2S,3S)-2,6-dimethyl-1-hydroxy-3-triethylsilanyloxyhepta-6-enyl]acrylic acid p-methoxybenzyl ester

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Chemical Name:(-)-2-[(2S,3S)-2,6-dimethyl-1-hydroxy-3-triethylsilanyloxyhepta-6-enyl]acrylic acid p-methoxybenzyl ester
CAS No.:1370458-37-9
Molecular Formula:C₂₆H₄₂O₅Si
Molecular Weight:462.702
Hs Code.:

Synonyms:(-)-2-[(2S,3S)-2,6-dimethyl-1-hydroxy-3-triethylsilanyloxyhepta-6-enyl]acrylic acid p-methoxybenzyl ester

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Chemical Property of (-)-2-[(2S,3S)-2,6-dimethyl-1-hydroxy-3-triethylsilanyloxyhepta-6-enyl]acrylic acid p-methoxybenzyl ester

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Technology Process of (-)-2-[(2S,3S)-2,6-dimethyl-1-hydroxy-3-triethylsilanyloxyhepta-6-enyl]acrylic acid p-methoxybenzyl ester

There total 6 articles about (-)-2-[(2S,3S)-2,6-dimethyl-1-hydroxy-3-triethylsilanyloxyhepta-6-enyl]acrylic acid p-methoxybenzyl 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: 88.0%

: 1370458-31-3
(-)-2-[(2S,3S)-2,6-dimethyl-1-hydroxy-3-triethylsilanyloxyhepta-6-enyl]-acrylic acid methyl ester

: 105-13-5
4-Methoxybenzyl alcohol

: 1370458-37-9
(-)-2-[(2S,3S)-2,6-dimethyl-1-hydroxy-3-triethylsilanyloxyhepta-6-enyl]acrylic acid p-methoxybenzyl ester

Guidance literature:: With Otera's catalyst; In toluene; at 110 ℃; for 13h;
DOI:10.1021/ol300615w

Reference yield:

: 1370458-47-1
C₁₁H₂₁NO₃

: 1370458-37-9
(-)-2-[(2S,3S)-2,6-dimethyl-1-hydroxy-3-triethylsilanyloxyhepta-6-enyl]acrylic acid p-methoxybenzyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: 1H-imidazole / dichloromethane / 5 h / 20 °C / Inert atmosphere

2.1: diisobutylaluminium hydride / hexane; toluene / 3 h / -78 °C / Inert atmosphere

3.1: N,N,N,N,N,N-hexamethylphosphoric triamide; diisobutylaluminium hydride / tetrahydrofuran; hexane / 1 h / 0 °C / Inert atmosphere

3.2: 5 h / 0 - 20 °C / Inert atmosphere

4.1: Otera's catalyst / toluene / 13 h / 110 °C

With 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; Otera's catalyst; diisobutylaluminium hydride; In tetrahydrofuran; hexane; dichloromethane; toluene;
DOI:10.1021/ol300615w

Reference yield:

: 3973-43-1
4-methylpent-4-enal

: 1370458-37-9
(-)-2-[(2S,3S)-2,6-dimethyl-1-hydroxy-3-triethylsilanyloxyhepta-6-enyl]acrylic acid p-methoxybenzyl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: di-n-butylboryl trifluoromethanesulfonate; triethylamine / dichloromethane / 0.17 h / -78 - 0 °C / Inert atmosphere

1.2: -78 - 0 °C / Inert atmosphere

2.1: trimethylaluminum / tetrahydrofuran; hexane / 1 h / 0 - 20 °C / Inert atmosphere

2.2: 2 h / 0 °C / Inert atmosphere

3.1: 1H-imidazole / dichloromethane / 5 h / 20 °C / Inert atmosphere

4.1: diisobutylaluminium hydride / hexane; toluene / 3 h / -78 °C / Inert atmosphere

5.1: N,N,N,N,N,N-hexamethylphosphoric triamide; diisobutylaluminium hydride / tetrahydrofuran; hexane / 1 h / 0 °C / Inert atmosphere

5.2: 5 h / 0 - 20 °C / Inert atmosphere

6.1: Otera's catalyst / toluene / 13 h / 110 °C

With 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; Otera's catalyst; di-n-butylboryl trifluoromethanesulfonate; trimethylaluminum; diisobutylaluminium hydride; triethylamine; In tetrahydrofuran; hexane; dichloromethane; toluene; 1.1: Evans Aldo reaction;
DOI:10.1021/ol300615w