Cholesteryl ether

Base Information

• Chemical Name: Cholesteryl ether
• CAS No.: 2469-23-0
• Molecular Formula: C54H90 O
• Molecular Weight: 755.308
• NSC Number: 167402
• DSSTox Substance ID: DTXSID30947631
• Mol file: 2469-23-0.mol

Synonyms:Cholesteryl ether;2469-23-0;3,3'-Oxybischolest-5-ene (3beta)-(3'beta)-;Cholest-5-ene, 3,3'-oxybis-, (3beta)-(3'beta)-;NSC 167402;3,3'-Oxydi(cholest-5-ene);DTXSID30947631;NSC167402;NSC-167402;Cholest-5-ene,3'-oxybis-, (3.beta.)-(3'.beta.)-

Chemical Property of Cholesteryl ether

Chemical Property:

• Boiling Point: 742.6°Cat760mmHg
• Flash Point: 412.6°C
• PSA: 9.23000
• Density: 0.99g/cm³
• LogP: 15.82300
• XLogP3: 18.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 12
• Exact Mass: 754.69916749
• Heavy Atom Count: 55
• Complexity: 1300

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)CCCC(C)C1CCC2C1(CCC3C2CC=C4C3(CCC(C4)OC5CCC6(C7CCC8(C(C7CC=C6C5)CCC8C(C)CCCC(C)C)C)C)C)C

Technology Process of Cholesteryl ether

There total 16 articles about Cholesteryl 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: 69.0%

cholesterol (57-88-5) → cholesteryl chloride (910-31-6) + dicholesteryl ether (2469-23-0)

Guidance literature:

With iron(III) chloride; In dichloromethane; at 20 ℃; for 5h;

DOI:10.1016/j.steroids.2005.04.008

Reference yield: 61.0%

i-cholesteryl methyl ether (2867-93-8,60175-48-6,84985-77-3,103365-95-3,122406-68-2) → cholesterol (57-88-5) + cholesteryl methyl ether (1174-92-1) + dicholesteryl ether (2469-23-0)

Guidance literature:

With trifluorormethanesulfonic acid; water; In 1,4-dioxane; at 20 ℃; for 5h;

DOI:10.1016/j.chemphyslip.2015.12.003

Reference yield: 47.0%

3,5-cyclocholesterol (465-54-3) + 1,2:3,4-di-O-isopropylidene-α-D-galactopyranose (4064-06-6) → 3β-O-(1’,2’:3’,4’-di-O-isopropylidene-α-D-galactopyranos-6’-yl)cholest-5-ene (1232680-84-0) + cholesterol (57-88-5) + dicholesteryl ether (2469-23-0)

Guidance literature:

With tetrabutylammonium tetrafluoroborate; In dichloromethane; acetonitrile; at 25 ℃; for 1.11111h; Molecular sieve; Electrochemical reaction; Inert atmosphere;

DOI:10.3762/bjoc.11.16

upstream raw materials:

cholesterol

salicylic acid

2,3,4,6-tetra-O-acetyl-D-glucopyranosyl bromide

cholesterol

Downstream raw materials:

cholesteryl iso-amyl ether

3-β-Fluorocholest-5-ene

Refernces

• 1、 Tomkiel, Aneta M.,Biedrzycki, Adam,Ploszyska, Jolanta,Narg, Dorota,Sobkowiak, Andrzej,Morzycki, Jacek W.. "3α,5α-Cyclocholestan-6β-yl ethers as donors of the holesterol moiety for the electrochemical synthesis f cholesterol glycoconjugates". supporting information. p. 162 - 168. Retrieved 2015/02/05.
• 2、 Morzycki, Jacek W.,?otowski, Zenon,Siergiejczyk, Leszek,Wa?ejko, Piotr,Witkowski, Stanis?aw,Kowalski, Jan,P?oszyn?ska, Jolanta,Sobkowiak, Andrzej. "A selective electrochemical method of glycosylation of 3β-hydroxy-Δ5-steroids". experimental part. p. 1051 - 1055. Retrieved 2010/08/20.