(3R,1'R,2'S)-3-triisopropylsilanyloxybutyric acid 2-hydroxy-1-methyl-2-phenylethyl ester

Base Information

Chemical Name:(3R,1'R,2'S)-3-triisopropylsilanyloxybutyric acid 2-hydroxy-1-methyl-2-phenylethyl ester
CAS No.:873196-79-3
Molecular Formula:C₂₂H₃₈O₄Si
Molecular Weight:394.627
Hs Code.:

Synonyms:(3R,1'R,2'S)-3-triisopropylsilanyloxybutyric acid 2-hydroxy-1-methyl-2-phenylethyl ester

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Chemical Property of (3R,1'R,2'S)-3-triisopropylsilanyloxybutyric acid 2-hydroxy-1-methyl-2-phenylethyl ester

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Technology Process of (3R,1'R,2'S)-3-triisopropylsilanyloxybutyric acid 2-hydroxy-1-methyl-2-phenylethyl ester

There total 5 articles about (3R,1'R,2'S)-3-triisopropylsilanyloxybutyric acid 2-hydroxy-1-methyl-2-phenylethyl 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: 51.0%

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

: 873196-79-3
(3R,1'R,2'S)-3-triisopropylsilanyloxybutyric acid 2-hydroxy-1-methyl-2-phenylethyl ester

Guidance literature:: With sodium dihydrogenphosphate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 20 ℃; for 48h;
DOI:10.1021/jo051930+

Reference yield:

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

: 873196-79-3
(3R,1'R,2'S)-3-triisopropylsilanyloxybutyric acid 2-hydroxy-1-methyl-2-phenylethyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 84 percent / chiral phosphoramide catalyst / CH₂Cl₂ / 6 h / -68 °C

2: 51 percent / m-chloroperbenzoic acid; NaH₂PO₄ / CH₂Cl₂ / 48 h / 20 °C

With sodium dihydrogenphosphate; chiral phosphoramide catalyst; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; 1: aldol addition;
DOI:10.1021/jo051930+

Reference yield:

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

: 873196-79-3
(3R,1'R,2'S)-3-triisopropylsilanyloxybutyric acid 2-hydroxy-1-methyl-2-phenylethyl ester

Guidance literature:: Multi-step reaction with 4 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

4.1: 51 percent / m-chloroperbenzoic acid; NaH₂PO₄ / CH₂Cl₂ / 48 h / 20 °C

With sodium dihydrogenphosphate; n-butyllithium; chiral phosphoramide catalyst; N-tert-butyl-N-tritylamine; methyllithium; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; 3.1: aldol addition;
DOI:10.1021/jo051930+