cinatrin C1

Base Information

• Chemical Name: cinatrin C1
• CAS No.: 136266-35-8
• Molecular Formula: C₁₈H₃₀O₈
• Molecular Weight: 374.431
• Mol file: 136266-35-8.mol

Synonyms:Cinatrin C1

Chemical Property of cinatrin C1

Chemical Property:

• Vapor Pressure: 2.36E-13mmHg at 25°C
• Boiling Point: 528°Cat760mmHg
• Flash Point: 181.2°C
• PSA: 119.36000
• Density: 1.203g/cm³
• LogP: 2.36920

Purity/Quality:

CINATRIN C1 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of cinatrin C1

There total 38 articles about cinatrin C1 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: 89.0%

benzyl-(3R,4S,5S)-2-oxo-3,4-dihydroxy-4-carboxy-5-dodecyl-tetrahydrofuran-5-carboxylate (193957-74-3) → (+)-cinatrin C1 (136266-35-8)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; for 0.666667h;

DOI:10.1016/S0040-4020(97)90390-2

Reference yield: 36.0%

cinatrin C1 dimethyl ester (136266-39-2) → cinatrin C1 (136266-35-8) + cinatrin C3 (136266-37-0)

Guidance literature:

cinatrin C₁ dimethyl ester; With sodium hydroxide; In tetrahydrofuran; at 40 ℃; for 22h;

With hydrogenchloride; In tetrahydrofuran; at 20 - 40 ℃; for 4.5h; Further stages.;

DOI:10.1039/b308028e

Reference yield: 22.0%

di-tert-butyl-(2S,3R)-2((1S)-1-carboxy-1-hydroxydodecyl)-1,4-dioxaspiro[4.4]nonane-2,3-dicarboxylate → (+)-cinatrin C1 (136266-35-8) + (-)-cinatrin C3 (136266-37-0)

Guidance literature:

In dichloromethane; water; trifluoroacetic acid; for 12h; Ambient temperature;

DOI:10.1016/S0040-4020(97)90390-2

upstream raw materials:

benzyl-(3R,4S,5S)-2-oxo-3,4-dihydroxy-4-carboxy-5-dodecyl-tetrahydrofuran-5-carboxylate

benzyl Myristate

benzyl-2-oxo-tetradecanoate

benzyl-2-hydroxytetradecanoate

Refernces

• 1、 Urabe, Fumiya,Nagashima, Shunsuke,Takahashi, Keisuke,Ishihara, Jun,Hatakeyama, Susumi. "Total synthesis of (-)-cinatrin C1 based on an In(OTf) 3-catalyzed Conia-ene reaction". . p. 3847 - 3857. Retrieved 2013/06/05.
• 2、 Evans, David A.,Trotter, B. Wesley,Barrow, James C.. "Aldol reactions of ketal-protected tartrate ester enolates. Asymmetric syntheses and absolute stereochemical assignments of phospholipase A2 inhibitors cinatrin C1 and C3". . p. 8779 - 8794. Retrieved 2007/10/03.