22-Keto-21-thia-3,6,9-trioxatricosan-1-OL

Base Information

• Chemical Name: 22-Keto-21-thia-3,6,9-trioxatricosan-1-OL
• CAS No.: 130727-50-3
• Molecular Formula: C19H38O5S
• Molecular Weight: 378.574
• DSSTox Substance ID: DTXSID00393282
• Nikkaji Number: J2.190.122I
• Wikidata: Q82192005
• Mol file: 130727-50-3.mol

Synonyms:22-KETO-21-THIA-3,6,9-TRIOXATRICOSAN-1-OL;130727-50-3;S-[11-[2-[2-(2-hydroxyethoxy)ethoxy]ethoxy]undecyl] ethanethioate;S-(11-(2-(2-(2-Hydroxyethoxy)ethoxy)ethoxy)undecyl) ethanethioate;starbld0008126;SCHEMBL1469721;DTXSID00393282;YDADHEIFTCDFFX-UHFFFAOYSA-N;FT-0670673;J-005864;2-[2-[2-[11-(Acetylthio)undecyloxy]ethoxy]ethoxy]ethanol;Thioacetic Acid S-(11-{2-[2-(2-hydroxyethoxy)ethoxy]ethoxy}undecyl)Ester

Chemical Property of 22-Keto-21-thia-3,6,9-trioxatricosan-1-OL

Chemical Property:

• PSA: 90.29000
• LogP: 3.81910
• Solubility.: Chloroform, Dichloromethane, Ethyl Acetate, Methanol
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 21
• Exact Mass: 378.24399548
• Heavy Atom Count: 25
• Complexity: 277

Purity/Quality:

99.90% ^*data from raw suppliers

22-Keto-21-thia-3,6,9-trioxatricosan-1-ol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)SCCCCCCCCCCCOCCOCCOCCO
• Uses: 22-Keto-21-thia-3,6,9-trioxatricosan-1-ol (cas# 130727-50-3) is a compound useful in organic synthesis.

Technology Process of 22-Keto-21-thia-3,6,9-trioxatricosan-1-OL

There total 5 articles about 22-Keto-21-thia-3,6,9-trioxatricosan-1-OL 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: 100.0%

2-(2-(2-(undec-10-enyloxy)ethoxy)ethoxy)ethanol (130727-45-6) + tiolacetic acid (507-09-5) → <1-<(methylcarbonyl)thio>undec-11-yl>tri(ethylene glycol) (130727-50-3)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); In tetrahydrofuran; at 20 ℃; for 3h; Inert atmosphere; UV-irradiation;

DOI:10.1002/chem.200902693

Reference yield: 93.0%

11-(bromoundecyl)triethylene glycol (860305-09-5) + tiolacetic acid (507-09-5) → <1-<(methylcarbonyl)thio>undec-11-yl>tri(ethylene glycol) (130727-50-3)

Guidance literature:

With sodium hydride; In methanol; at 20 ℃; for 96h;

DOI:10.1016/j.tetlet.2005.04.091

Reference yield:

1-undecen-11-ylbromide (7766-50-9) → <1-<(methylcarbonyl)thio>undec-11-yl>tri(ethylene glycol) (130727-50-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 70 percent / aq. NaOH / 24 h / 100 °C

2: 72 percent / AIBN / tetrahydrofuran / 12 h / Heating

With sodium hydroxide; 2,2'-azobis(isobutyronitrile); In tetrahydrofuran;

DOI:10.1002/chem.200204544

upstream raw materials:

2-(2-(2-(undec-10-enyloxy)ethoxy)ethoxy)ethanol

tiolacetic acid

11-(bromoundecyl)triethylene glycol

1,11-dibromoundecane

Downstream raw materials:

(1-mercaptoundec-11-yl)tri(ethylene glycol)

Refernces

• 1、 Kopitzki, Sebastian,Jensen, Knud J.,Thiem, Joachim. "Synthesis of benzaldehyde-functionalized glycans: A novel approach towards glyco-SAMs as a tool for surface plasmon resonance studies". experimental part. p. 7017 - 7029. Retrieved 2010/09/10.
• 2、 Barrientos, Africa G.,De la Fuente, Jesus M.,Rojas, Teresa C.,Fernandez, Asuncion,Penades, Soledad. "Gold glyconanoparticles: Synthetic polyvalent ligands mimicking glycocalyx-like surfaces as tools for glycobiological studies". . p. 1909 - 1921. Retrieved 2007/10/03.