acetic acid (1R,4S)-(-)-(tert-butyldimethylsiloxy)cyclohex-2-enyl ester

Base Information

• Chemical Name: acetic acid (1R,4S)-(-)-(tert-butyldimethylsiloxy)cyclohex-2-enyl ester
• CAS No.: 164414-39-5
• Molecular Formula: C₁₄H₂₆O₃Si
• Molecular Weight: 270.444
• Mol file: 164414-39-5.mol

Synonyms:acetic acid (1R,4S)-(-)-(tert-butyldimethylsiloxy)cyclohex-2-enyl ester

Chemical Property of acetic acid (1R,4S)-(-)-(tert-butyldimethylsiloxy)cyclohex-2-enyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of acetic acid (1R,4S)-(-)-(tert-butyldimethylsiloxy)cyclohex-2-enyl ester

There total 3 articles about acetic acid (1R,4S)-(-)-(tert-butyldimethylsiloxy)cyclohex-2-enyl 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: 99.0%

acetic acid (1S,4R)-(-)-4-hydroxycyclohex-2-enyl ester (132617-05-1) + tert-butyldimethylsilyl chloride (18162-48-6) → acetic acid (1R,4S)-(-)-(tert-butyldimethylsiloxy)cyclohex-2-enyl ester (164414-39-5)

Guidance literature:

With 1H-imidazole; In dichloromethane; 1.) 0 deg C, 30 min, 2.) r.t., 20 h;

DOI:10.1039/a600779a

Reference yield:

Acetic acid (1S,4R)-2,3-dibromo-4-hydroxy-cyclohexyl ester → acetic acid (1R,4S)-(-)-(tert-butyldimethylsiloxy)cyclohex-2-enyl ester (164414-39-5)

Guidance literature:

Multi-step reaction with 2 steps

1: Zn / ethanol / Heating

2: imidazole / CH₂Cl₂ / 25 °C

With 1H-imidazole; zinc; In ethanol; dichloromethane;

DOI:10.1021/ol050339w

Reference yield:

cyclohexa-1,3-diene (1165952-91-9) → acetic acid (1R,4S)-(-)-(tert-butyldimethylsiloxy)cyclohex-2-enyl ester (164414-39-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) LiCl, MnO₂, LiOAc, PBQ, Pd(OAc)2, 2.) Br₂, 3.) CCL, 4.) Zn

2: 82 percent / imidazole / dimethylformamide / 15 h / 37 °C

With 1H-imidazole; manganese(IV) oxide; palladium diacetate; lithium acetate; bromine; lithium chloride; zinc; In N,N-dimethyl-formamide;

DOI:10.1055/s-1997-1492

upstream raw materials:

acetic acid (1S,4R)-(-)-4-hydroxycyclohex-2-enyl ester

tert-butyldimethylsilyl chloride

cyclohexa-1,3-diene

Downstream raw materials:

cis-(1S,4R)-4-(tert-butyldimethylsilyloxy)cyclohex-2-enol

(2R,3R,4R)-(-)-4-(tert-butyldimethylsiloxy)-2,3-dimethylcyclohexanone

Acetic acid (1R,4R)-4-benzylamino-cyclohex-2-enyl ester

Acetic acid (1R,4R)-4-diethylamino-cyclohex-2-enyl ester