(3S,4R,5S)-2-Bromo-3-hydroxy-5-methoxy-2,4-dimethyl-5-phenyl-pentanoic acid ethyl ester

Base Information

Chemical Name:(3S,4R,5S)-2-Bromo-3-hydroxy-5-methoxy-2,4-dimethyl-5-phenyl-pentanoic acid ethyl ester
CAS No.:468729-23-9
Molecular Formula:C₁₆H₂₃BrO₄
Molecular Weight:359.26
Hs Code.:

Synonyms:(3S,4R,5S)-2-Bromo-3-hydroxy-5-methoxy-2,4-dimethyl-5-phenyl-pentanoic acid ethyl ester

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Chemical Property of (3S,4R,5S)-2-Bromo-3-hydroxy-5-methoxy-2,4-dimethyl-5-phenyl-pentanoic acid ethyl ester

Chemical Property:

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Technology Process of (3S,4R,5S)-2-Bromo-3-hydroxy-5-methoxy-2,4-dimethyl-5-phenyl-pentanoic acid ethyl ester

There total 3 articles about (3S,4R,5S)-2-Bromo-3-hydroxy-5-methoxy-2,4-dimethyl-5-phenyl-pentanoic acid ethyl 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: 73.0%

: 535-11-5,41978-69-2
Ethyl 2-bromopropionate

: 468729-16-0
(2S,3S)-3-methoxy-2-methyl-3-phenylpropanal

: (3R,4R,5S)-2-Bromo-3-hydroxy-5-methoxy-2,4-dimethyl-5-phenyl-pentanoic acid ethyl ester

: 468729-23-9
(3S,4R,5S)-2-Bromo-3-hydroxy-5-methoxy-2,4-dimethyl-5-phenyl-pentanoic acid ethyl ester

Guidance literature:: Ethyl 2-bromopropionate; With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; for 0.25h;

With chloro-trimethyl-silane; In tetrahydrofuran; at -78 - 20 ℃;

(2S,3S)-3-methoxy-2-methyl-3-phenylpropanal; With titanium tetrachloride; In dichloromethane; at -78 ℃; for 1.08333h;
DOI:10.1016/j.tetasy.2003.06.005

Reference yield:

: 630117-47-4
ethyl (2S,3S)-3-methoxy-2-methyl-3-phenylpropionate

: 468729-23-9
(3S,4R,5S)-2-Bromo-3-hydroxy-5-methoxy-2,4-dimethyl-5-phenyl-pentanoic acid ethyl ester

Guidance literature:: Multi-step reaction with 2 steps

1.1: DIBAL / CH₂Cl₂; toluene / 2.5 h / -78 °C

2.1: LDA / tetrahydrofuran / 0.25 h / -78 °C

2.2: Me₃SiCl / tetrahydrofuran / -78 - 20 °C

2.3: 73 percent / TiCl₄ / CH₂Cl₂ / 1.08 h / -78 °C

With diisobutylaluminium hydride; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; toluene;
DOI:10.1016/j.tetasy.2003.06.005

Reference yield:

: ethyl (3R)-2-bromo-3-hydroxy-2-methyl-3-phenylpropionate

: 468729-23-9
(3S,4R,5S)-2-Bromo-3-hydroxy-5-methoxy-2,4-dimethyl-5-phenyl-pentanoic acid ethyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: Bu₃SnH; Et₃B / CH₂Cl₂; tetrahydrofuran / -78 °C

2.1: CH₂Cl₂ / 16 h / 20 °C

3.1: DIBAL / CH₂Cl₂; toluene / 2.5 h / -78 °C

4.1: LDA / tetrahydrofuran / 0.25 h / -78 °C

4.2: Me₃SiCl / tetrahydrofuran / -78 - 20 °C

4.3: 73 percent / TiCl₄ / CH₂Cl₂ / 1.08 h / -78 °C

With triethyl borane; tri-n-butyl-tin hydride; diisobutylaluminium hydride; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; toluene;
DOI:10.1016/j.tetasy.2003.06.005