(1R,2R,5S)-5-triisopropylsilyloxy-2-methyl-1-hydroxy-1-phenyl-3-hexanone

Base Information

Chemical Name:(1R,2R,5S)-5-triisopropylsilyloxy-2-methyl-1-hydroxy-1-phenyl-3-hexanone
CAS No.:474826-55-6
Molecular Formula:C₂₂H₃₈O₃Si
Molecular Weight:378.627
Hs Code.:

Synonyms:(1R,2R,5S)-5-triisopropylsilyloxy-2-methyl-1-hydroxy-1-phenyl-3-hexanone

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (1R,2R,5S)-5-triisopropylsilyloxy-2-methyl-1-hydroxy-1-phenyl-3-hexanone

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Technology Process of (1R,2R,5S)-5-triisopropylsilyloxy-2-methyl-1-hydroxy-1-phenyl-3-hexanone

There total 4 articles about (1R,2R,5S)-5-triisopropylsilyloxy-2-methyl-1-hydroxy-1-phenyl-3-hexanone 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: 84.0%

: 474826-34-1
(2Z,5S)-5-triisopropylsilyloxy-3-trichlorosilyloxy-2-hexene

: 100-52-7
benzaldehyde

: 474826-55-6
(1R,2R,5S)-5-triisopropylsilyloxy-2-methyl-1-hydroxy-1-phenyl-3-hexanone

Guidance literature:: With chiral phosphoramide catalyst; In dichloromethane; at -68 ℃; for 6h;
DOI:10.1021/jo051930+

Reference yield:

: 474826-12-5
(S)-5-triisopropylsilyloxy-3-hexanone

: 474826-55-6
(1R,2R,5S)-5-triisopropylsilyloxy-2-methyl-1-hydroxy-1-phenyl-3-hexanone

Guidance literature:: Multi-step reaction with 3 steps

1.1: 69 percent / tert-butyl-tritylamine; n-BuLi / tetrahydrofuran; hexane / 2.5 h / -78 - 0 °C

2.1: MeLi / diethyl ether; tetrahydrofuran / 4.5 h / 20 °C

2.2: SiCl₄ / diethyl ether; tetrahydrofuran / 1 h / -70 °C

3.1: 84 percent / chiral phosphoramide catalyst / CH₂Cl₂ / 6 h / -68 °C

With n-butyllithium; chiral phosphoramide catalyst; N-tert-butyl-N-tritylamine; methyllithium; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; 3.1: aldol addition;
DOI:10.1021/jo051930+

Reference yield:

: 474826-23-8
(2E,5S)-5-triisopropylsilyloxy-3-trimethylsilyloxy-2-hexene

: 474826-55-6
(1R,2R,5S)-5-triisopropylsilyloxy-2-methyl-1-hydroxy-1-phenyl-3-hexanone

Guidance literature:: Multi-step reaction with 2 steps

1.1: MeLi / diethyl ether; tetrahydrofuran / 4.5 h / 20 °C

1.2: SiCl₄ / diethyl ether; tetrahydrofuran / 1 h / -70 °C

2.1: 84 percent / chiral phosphoramide catalyst / CH₂Cl₂ / 6 h / -68 °C

With chiral phosphoramide catalyst; methyllithium; In tetrahydrofuran; diethyl ether; dichloromethane; 2.1: aldol addition;
DOI:10.1021/jo051930+