9-cis-(tert-Butyldimethylsilyl)retinyl Ether

Base Information

• Chemical Name: 9-cis-(tert-Butyldimethylsilyl)retinyl Ether
• CAS No.: 210700-52-0
• Molecular Formula: C26H44 O Si
• Molecular Weight: 400.72
• Mol file: 210700-52-0.mol

Synonyms:(1,1-Dimethylethyl)[[(2E,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethyl -1-cyclohexen-1-yl)-2,4,6,8-nonatetraenyl]oxy]dimethylsilane;9-cis-(tert-Butyldimethylsilyl)retinyl Ether

Chemical Property of 9-cis-(tert-Butyldimethylsilyl)retinyl Ether

Chemical Property:

• Vapor Pressure: 1.77E-08mmHg at 25°C
• Refractive Index: 1.507
• Boiling Point: 467.8°C at 760 mmHg
• Flash Point: 246.3°C
• PSA: 9.23000
• Density: 0.903g/cm³
• LogP: 8.53980
• Solubility.: Dichloromethane, Ethyl Acetate, Hexane

Purity/Quality:

98%Min ^*data from raw suppliers

9-cis-(tert-Butyldimethylsilyl)retinylEther ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Intermediate for the synthesis of 9-cis-Retinoids

Technology Process of 9-cis-(tert-Butyldimethylsilyl)retinyl Ether

There total 2 articles about 9-cis-(tert-Butyldimethylsilyl)retinyl Ether 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: 67.0%

tert-butyldimethylsilyl (7E,9Z,11Z,13E)-12-(phenylsulfinyl)retinyl ether (210700-50-8) → tert-butyldimethylsilyl (7E,9Z,11E,13E)-retinyl ether (210700-52-0)

Guidance literature:

With methanol; methyllithium; tert.-butyl lithium; In tetrahydrofuran; diethyl ether; pentane; at -78 ℃; for 0.166667h; rate of RLi addition is 2.1 mL/h;

DOI:10.1021/jo991757f

Reference yield:

(2E,7E)-9-(tert-Butyl-dimethyl-silanyloxy)-3,7-dimethyl-1-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,7-dien-5-yn-4-ol (154307-85-4) → tert-butyldimethylsilyl (7E,9Z,11E,13E)-retinyl ether (210700-52-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 61 percent / Et₃N / tetrahydrofuran / -78 - 25 °C

2: 67 percent / MeLi; t-BuLi; MeOH / tetrahydrofuran; diethyl ether; pentane / 0.17 h / -78 °C / rate of RLi addition is 2.1 mL/h

With methanol; methyllithium; tert.-butyl lithium; triethylamine; In tetrahydrofuran; diethyl ether; pentane; 1: Addition / 2: desulfuration;

DOI:10.1021/jo991757f

Reference yield: 93.0%

tert-butyldimethylsilyl (7E,9Z,11E,13E)-retinyl ether (210700-52-0) → 9-cis-retinol (68-26-8,2052-63-3,6018-74-2,17706-49-9,22737-96-8,29444-25-5,34218-73-0,39815-04-8,69686-68-6,69686-69-7,74743-94-5,84415-27-0,84415-28-1,85354-09-2,85354-10-5,93380-02-0,98462-62-5,137121-52-9,22737-97-9)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 25 ℃; for 1.5h;

DOI:10.1021/jo991757f

upstream raw materials:

tert-butyldimethylsilyl (7E,9Z,11Z,13E)-12-(phenylsulfinyl)retinyl ether

(2E,7E)-9-(tert-Butyl-dimethyl-silanyloxy)-3,7-dimethyl-1-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,7-dien-5-yn-4-ol

Downstream raw materials:

9-cis-retinol

9-cis-retinoic acid

Refernces