(Z)-4-(triisopropylsiloxy)-2-butenyloxy acetic acid (-)-menthyl ester

Base Information

• Chemical Name: (Z)-4-(triisopropylsiloxy)-2-butenyloxy acetic acid (-)-menthyl ester
• CAS No.: 223384-51-8
• Molecular Formula: C₂₅H₄₈O₄Si
• Molecular Weight: 440.739
• Mol file: 223384-51-8.mol

Synonyms:(Z)-4-(triisopropylsiloxy)-2-butenyloxy acetic acid (-)-menthyl ester

Chemical Property of (Z)-4-(triisopropylsiloxy)-2-butenyloxy acetic acid (-)-menthyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z)-4-(triisopropylsiloxy)-2-butenyloxy acetic acid (-)-menthyl ester

There total 3 articles about (Z)-4-(triisopropylsiloxy)-2-butenyloxy acetic acid (-)-menthyl 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: 93.0%

(-)-menthol (2216-51-5) + (Z)-4-(triisopropylsiloxy)-2-butenyloxy acetic acid (223384-50-7) → (Z)-4-(triisopropylsiloxy)-2-butenyloxy acetic acid (-)-menthyl ester (223384-51-8)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 0 ℃;

DOI:10.1016/S0040-4020(99)00019-8

Reference yield:

triisopropylsilyl chloride (13154-24-0) → (Z)-4-(triisopropylsiloxy)-2-butenyloxy acetic acid (-)-menthyl ester (223384-51-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 90 percent / imidazole / tetrahydrofuran / 8 h / Ambient temperature

2: 67 percent / NaH / tetrahydrofuran / 1.) 25 deg C, 2 h, 2.) reflux, 1 h

3: 93 percent / DCC, DMAP / CH₂Cl₂ / 0 °C

With 1H-imidazole; dmap; sodium hydride; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane;

DOI:10.1016/S0040-4020(99)00019-8

Reference yield:

(Z)-4-[(triisopropylsilyl)oxy]-2-buten-1-ol (178905-41-4) → (Z)-4-(triisopropylsiloxy)-2-butenyloxy acetic acid (-)-menthyl ester (223384-51-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 67 percent / NaH / tetrahydrofuran / 1.) 25 deg C, 2 h, 2.) reflux, 1 h

2: 93 percent / DCC, DMAP / CH₂Cl₂ / 0 °C

With dmap; sodium hydride; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane;

DOI:10.1016/S0040-4020(99)00019-8

upstream raw materials:

(-)-menthol

(Z)-4-(triisopropylsiloxy)-2-butenyloxy acetic acid

triisopropylsilyl chloride

(Z)-4-[(triisopropylsilyl)oxy]-2-buten-1-ol

Downstream raw materials:

(2RS)-(3,4-dihydro-naphthalen-1-yl)-<(Z)-4-triisopropylsiloxy-but-2-enyloxy>-acetic acid (-)-menthyl ester

(2RS)-(1-hydroxy-1,2,3,4-tetrahydro-naphthalen-1-yl)-<(Z)-4-triisopropylsiloxy-but-2-enyloxy>-acetic acid (-)-menthyl ester

(2RS)-(1-hydroxy-cyclopentyl)-<(Z)-4-triisopropylsiloxy-but-2-enyloxy>-acetic acid (-)-menthyl ester

(2RS)-3-hydroxy-3-methyl-2-<(Z)-4-(triisopropylsiloxy)-but-2-enyloxy>-butyric acid (-)-menthyl ester