(E)-(2S,3R)-methyl 2-(4-methoxybenzyloxy)-3-(dimethylphenylsilyl)-3-methyl-hex-4-enoate

Base Information

• Chemical Name: (E)-(2S,3R)-methyl 2-(4-methoxybenzyloxy)-3-(dimethylphenylsilyl)-3-methyl-hex-4-enoate
• CAS No.: 851760-05-9
• Molecular Formula: C₂₄H₃₂O₄Si
• Molecular Weight: 412.601
• Mol file: 851760-05-9.mol

Synonyms:(E)-(2S,3R)-methyl 2-(4-methoxybenzyloxy)-3-(dimethylphenylsilyl)-3-methyl-hex-4-enoate

Chemical Property of (E)-(2S,3R)-methyl 2-(4-methoxybenzyloxy)-3-(dimethylphenylsilyl)-3-methyl-hex-4-enoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-(2S,3R)-methyl 2-(4-methoxybenzyloxy)-3-(dimethylphenylsilyl)-3-methyl-hex-4-enoate

There total 5 articles about (E)-(2S,3R)-methyl 2-(4-methoxybenzyloxy)-3-(dimethylphenylsilyl)-3-methyl-hex-4-enoate 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%

(E)-(2S,3R)-3-(dimethyl-phenyl-silanyl)-2-(4-methoxy-benzyloxy)-3-methyl-hex-4-enoic acid (851759-73-4) + methyl iodide (74-88-4) → (E)-(2S,3R)-methyl 2-(4-methoxybenzyloxy)-3-(dimethylphenylsilyl)-3-methyl-hex-4-enoate (851760-05-9)

Guidance literature:

With Adogen-464(R); sodium hydrogencarbonate; In dichloromethane; at 20 ℃;

DOI:10.1021/ol0501875

Reference yield:

(Z)-(R)-4-(dimethyl-phenyl-silanyl)-pent-3-en-2-ol (851759-94-9) → (E)-(2S,3R)-methyl 2-(4-methoxybenzyloxy)-3-(dimethylphenylsilyl)-3-methyl-hex-4-enoate (851760-05-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 80 percent / DCC; DMAP / CH₂Cl₂ / 0 - 20 °C

2.1: LiHMDS / tetrahydrofuran / 0.5 h / -78 °C

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

3.1: 88 percent / NaHCO₃; Adogen-464(R) / CH₂Cl₂ / 20 °C

With dmap; Adogen-464(R); sodium hydrogencarbonate; dicyclohexyl-carbodiimide; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ol0501875

Reference yield:

(Z)-(R)-(3-iodo-1-methyl-but-2-enyloxy)-dimethyl-phenyl-silane (851760-04-8) → (E)-(2S,3R)-methyl 2-(4-methoxybenzyloxy)-3-(dimethylphenylsilyl)-3-methyl-hex-4-enoate (851760-05-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 90 percent / t-BuLi / tetrahydrofuran / 2 h / -78 °C

2.1: 80 percent / DCC; DMAP / CH₂Cl₂ / 0 - 20 °C

3.1: LiHMDS / tetrahydrofuran / 0.5 h / -78 °C

3.2: TMSCl / tetrahydrofuran / -78 - 20 °C

4.1: 88 percent / NaHCO₃; Adogen-464(R) / CH₂Cl₂ / 20 °C

With dmap; Adogen-464(R); tert.-butyl lithium; sodium hydrogencarbonate; dicyclohexyl-carbodiimide; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ol0501875

upstream raw materials:

(E)-(2S,3R)-3-(dimethyl-phenyl-silanyl)-2-(4-methoxy-benzyloxy)-3-methyl-hex-4-enoic acid

methyl iodide

(Z)-(R)-4-(dimethyl-phenyl-silanyl)-pent-3-en-2-ol

(Z)-(R)-(3-iodo-1-methyl-but-2-enyloxy)-dimethyl-phenyl-silane

Downstream raw materials:

(E)-(2S,3R)-methyl 3-(dimethylphenylsilyl)-3-methyl-2-(trimethyulsilyloxy)-hex-4-enoate

(E)-(2S,3R)-methyl 2-hydroxy-3-(dimethylphenylsilyl)-3-methyl-hex-4-enoate