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

Base Information

• Chemical Name: (2RS)-(1-hydroxy-1,2,3,4-tetrahydro-naphthalen-1-yl)-<(Z)-4-triisopropylsiloxy-but-2-enyloxy>-acetic acid (-)-menthyl ester
• CAS No.: 223384-54-1
• Molecular Formula: C₃₅H₅₈O₅Si
• Molecular Weight: 586.928
• Mol file: 223384-54-1.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 3 articles about (2RS)-(1-hydroxy-1,2,3,4-tetrahydro-naphthalen-1-yl)-<(Z)-4-triisopropylsiloxy-but-2-enyloxy>-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:

(Z)-4-[(triisopropylsilyl)oxy]-2-buten-1-ol (178905-41-4) → (2RS)-(1-hydroxy-1,2,3,4-tetrahydro-naphthalen-1-yl)-<(Z)-4-triisopropylsiloxy-but-2-enyloxy>-acetic acid (-)-menthyl ester (223384-54-1)

Guidance literature:

Multi-step reaction with 3 steps

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

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

3: 1.) LDA / 1.) THF, -78 deg C, 10 min, 2.) -78 deg C, 30 min

With dmap; sodium hydride; dicyclohexyl-carbodiimide; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane;

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

Reference yield:

(Z)-4-(triisopropylsiloxy)-2-butenyloxy acetic acid (223384-50-7) → (2RS)-(1-hydroxy-1,2,3,4-tetrahydro-naphthalen-1-yl)-<(Z)-4-triisopropylsiloxy-but-2-enyloxy>-acetic acid (-)-menthyl ester (223384-54-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 93 percent / DCC, DMAP / CH₂Cl₂ / 0 °C

2: 1.) LDA / 1.) THF, -78 deg C, 10 min, 2.) -78 deg C, 30 min

With dmap; dicyclohexyl-carbodiimide; lithium diisopropyl amide; In dichloromethane;

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

Reference yield:

3,4-dihydronaphthalene-1(2H)-one (529-34-0) + (Z)-4-(triisopropylsiloxy)-2-butenyloxy acetic acid (-)-menthyl ester (223384-51-8) → (2RS)-(1-hydroxy-1,2,3,4-tetrahydro-naphthalen-1-yl)-<(Z)-4-triisopropylsiloxy-but-2-enyloxy>-acetic acid (-)-menthyl ester (223384-54-1)

Guidance literature:

With lithium diisopropyl amide; Yield given; Multistep reaction; 1.) THF, -78 deg C, 10 min, 2.) -78 deg C, 30 min;

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

upstream raw materials:

3,4-dihydronaphthalene-1(2H)-one

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

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

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

Downstream raw materials:

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