(2S,3R)-2-(tert-Butyl-dimethyl-silanyloxy)-4-methyl-5-oxo-3-phenyl-pentanoic acid ethyl ester

Base Information

• Chemical Name: (2S,3R)-2-(tert-Butyl-dimethyl-silanyloxy)-4-methyl-5-oxo-3-phenyl-pentanoic acid ethyl ester
• CAS No.: 1027145-18-1
• Molecular Formula: C₂₀H₃₂O₄Si
• Molecular Weight: 364.557

Synonyms:(2S,3R)-2-(tert-Butyl-dimethyl-silanyloxy)-4-methyl-5-oxo-3-phenyl-pentanoic acid ethyl ester

Chemical Property of (2S,3R)-2-(tert-Butyl-dimethyl-silanyloxy)-4-methyl-5-oxo-3-phenyl-pentanoic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of (2S,3R)-2-(tert-Butyl-dimethyl-silanyloxy)-4-methyl-5-oxo-3-phenyl-pentanoic acid ethyl ester

There total 7 articles about (2S,3R)-2-(tert-Butyl-dimethyl-silanyloxy)-4-methyl-5-oxo-3-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:

(2-methyl-1-propenyl)-benzene (768-49-0) → (2S,3R)-2-(tert-Butyl-dimethyl-silanyloxy)-4-methyl-5-oxo-3-phenyl-pentanoic acid ethyl ester (1027145-18-1)

Guidance literature:

Multi-step reaction with 7 steps

1.1: SnCl₄ / CH₂Cl₂ / 2.5 h / -78 °C

1.2: 81 percent / 19 h / -25 °C

2.1: 90 percent / NaOH / tetrahydrofuran; methanol / 15 h / Heating

3.1: 79 percent / SOCl₂ / methanol / 4 h / Heating

4.1: 85 percent / 2,6-lutidine; DMAP / CH₂Cl₂ / 2.5 h / 20 °C

5.1: 9-borabicyclo[3.3.1]nonane / tetrahydrofuran / 3.5 h / 20 °C

5.2: 98 percent / NaOH; H₂O₂ / 0.5 h / sonication

6.1: DMSO; oxalyl chloride; NEt₃ / CH₂Cl₂ / 0.33 h / -78 °C

7.1: NaHCO₃ / 3 h / Heating

With 2,6-dimethylpyridine; dmap; sodium hydroxide; thionyl chloride; oxalyl dichloride; tin(IV) chloride; sodium hydrogencarbonate; dimethyl sulfoxide; triethylamine; 9-bora-bicyclo[3.3.1]nonane; In tetrahydrofuran; methanol; dichloromethane; 1.1: Whitesell ene reaction / 6.1: Swern oxidation;

DOI:10.1002/1099-0690(200209)2002:17<2905::AID-EJOC2905>3.0.CO;2-3

Reference yield:

methyl (2S,3R)-2-hydroxy-4-methyl-3-phenylpent-4-enoate (475503-85-6) → (2S,3R)-2-(tert-Butyl-dimethyl-silanyloxy)-4-methyl-5-oxo-3-phenyl-pentanoic acid ethyl ester (1027145-18-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 85 percent / 2,6-lutidine; DMAP / CH₂Cl₂ / 2.5 h / 20 °C

2.1: 9-borabicyclo[3.3.1]nonane / tetrahydrofuran / 3.5 h / 20 °C

2.2: 98 percent / NaOH; H₂O₂ / 0.5 h / sonication

3.1: DMSO; oxalyl chloride; NEt₃ / CH₂Cl₂ / 0.33 h / -78 °C

4.1: NaHCO₃ / 3 h / Heating

With 2,6-dimethylpyridine; dmap; oxalyl dichloride; sodium hydrogencarbonate; dimethyl sulfoxide; triethylamine; 9-bora-bicyclo[3.3.1]nonane; In tetrahydrofuran; dichloromethane; 3.1: Swern oxidation;

DOI:10.1002/1099-0690(200209)2002:17<2905::AID-EJOC2905>3.0.CO;2-3

Reference yield:

(2S,3R)-2-hydroxy-4-methyl-3-phenylpent-4-enoic acid (475503-84-5) → (2S,3R)-2-(tert-Butyl-dimethyl-silanyloxy)-4-methyl-5-oxo-3-phenyl-pentanoic acid ethyl ester (1027145-18-1)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 79 percent / SOCl₂ / methanol / 4 h / Heating

2.1: 85 percent / 2,6-lutidine; DMAP / CH₂Cl₂ / 2.5 h / 20 °C

3.1: 9-borabicyclo[3.3.1]nonane / tetrahydrofuran / 3.5 h / 20 °C

3.2: 98 percent / NaOH; H₂O₂ / 0.5 h / sonication

4.1: DMSO; oxalyl chloride; NEt₃ / CH₂Cl₂ / 0.33 h / -78 °C

5.1: NaHCO₃ / 3 h / Heating

With 2,6-dimethylpyridine; dmap; thionyl chloride; oxalyl dichloride; sodium hydrogencarbonate; dimethyl sulfoxide; triethylamine; 9-bora-bicyclo[3.3.1]nonane; In tetrahydrofuran; methanol; dichloromethane; 4.1: Swern oxidation;

DOI:10.1002/1099-0690(200209)2002:17<2905::AID-EJOC2905>3.0.CO;2-3

upstream raw materials:

ethanol

(2S,3R,4R)-2-(tert-Butyl-dimethyl-silanyloxy)-4-methyl-5-oxo-3-phenyl-pentanoic acid methyl ester

(2-methyl-1-propenyl)-benzene

methyl (2S,3R)-2-hydroxy-4-methyl-3-phenylpent-4-enoate

Downstream raw materials:

(2S,3R,4S)-2-hydroxy-4-methyl-3-phenyl-δ-valerolactone

(2S,3R,4S)-2-(tert-butyldimethylsilyloxy)-4-methyl-3-phenyl-δ-valerolactone

ethyl (2S,3R,4R)-2-(tert-butyldimethylsilyloxy)-5-hydroxy-4-methyl-3-phenylpentanoate

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