Methyl (4S,5Z,6S)-5-ethylidene-4-[2-[2-(4-hydroxyphenyl)ethoxy]-2-oxoethyl]-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4H-pyran-3-carboxylate

Base Information

• Chemical Name: Methyl (4S,5Z,6S)-5-ethylidene-4-[2-[2-(4-hydroxyphenyl)ethoxy]-2-oxoethyl]-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4H-pyran-3-carboxylate
• CAS No.: 35897-92-8
• Molecular Formula: C25H32O12
• Molecular Weight: 524.522
• Nikkaji Number: J1.671.128D
• Wikidata: Q76415581
• Mol file: 35897-92-8.mol

Synonyms:Methyl (4S,5Z,6S)-5-ethylidene-4-[2-[2-(4-hydroxyphenyl)ethoxy]-2-oxoethyl]-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4H-pyran-3-carboxylate;(8Z)-Ligstroside

Chemical Property of Methyl (4S,5Z,6S)-5-ethylidene-4-[2-[2-(4-hydroxyphenyl)ethoxy]-2-oxoethyl]-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4H-pyran-3-carboxylate

Chemical Property:

• Vapor Pressure: 8.5E-23mmHg at 25°C
• Refractive Index: 1.613
• Boiling Point: 736.9 °C at 760 mmHg
• PKA: 9.91±0.15(Predicted)
• Flash Point: 245.1 °C
• PSA: 181.44000
• Density: 1.44 g/cm³
• LogP: -0.33980
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: -0.1
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 11
• Exact Mass: 524.18937645
• Heavy Atom Count: 37
• Complexity: 834

Purity/Quality:

99% ^*data from raw suppliers

Ligustroside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC=C1C(C(=COC1OC2C(C(C(C(O2)CO)O)O)O)C(=O)OC)CC(=O)OCCC3=CC=C(C=C3)O
• Isomeric SMILES: C/C=C\1/[C@@H](C(=CO[C@H]1O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)C(=O)OC)CC(=O)OCCC3=CC=C(C=C3)O
• Uses: Ligustroside is a chemical constituent isolated from the flowers of Osmanthus fragrans var. aurantiacus which significantly inhibited nitric oxide production in lipopolysaccharide-activated RAW264.7 macrophages.

Technology Process of Methyl (4S,5Z,6S)-5-ethylidene-4-[2-[2-(4-hydroxyphenyl)ethoxy]-2-oxoethyl]-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4H-pyran-3-carboxylate

There total 7 articles about Methyl (4S,5Z,6S)-5-ethylidene-4-[2-[2-(4-hydroxyphenyl)ethoxy]-2-oxoethyl]-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4H-pyran-3-carboxylate 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: 71.0%

(2S,3S,4R,5S,6R)-2-(acetoxymethyl)-6-(((E)-3-ethylidene-4-(2-(4-hydroxyphenethoxy)-2-oxoethyl)-5-(methoxycarbonyl)-3,4-dihydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate → ligstroside (35897-92-8)

Guidance literature:

With diethylamine; In methanol; at 0 - 20 ℃; for 6h; Inert atmosphere;

DOI:10.1016/j.ejmech.2017.05.029

Reference yield:

4-carboxymethyl-5-ethylidene-6-(3,4,5-trihydroxy-6-hydroxymethyl-tetrahydropyran-2-yloxy)-5,6-dihydro-4H-pyran-3-carboxylic acid methyl ester (60539-23-3) → ligstroside (35897-92-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: pyridine / 2 h / 0 - 20 °C / Inert atmosphere

2.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / dichloromethane / 2 h / 0 - 20 °C

2.2: 2 h / 0 - 20 °C

3.1: diethylamine / methanol / 6 h / 0 - 20 °C / Inert atmosphere

With pyridine; 2,4,6-trichlorobenzoyl chloride; diethylamine; triethylamine; In methanol; dichloromethane;

DOI:10.1016/j.ejmech.2017.05.029

Reference yield:

oleuropeine (32619-42-4) → ligstroside (35897-92-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium hydroxide / water / 0.17 h / 100 °C / Microwave irradiation

2.1: pyridine / 2 h / 0 - 20 °C / Inert atmosphere

3.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / dichloromethane / 2 h / 0 - 20 °C

3.2: 2 h / 0 - 20 °C

4.1: diethylamine / methanol / 6 h / 0 - 20 °C / Inert atmosphere

With pyridine; 2,4,6-trichlorobenzoyl chloride; diethylamine; triethylamine; sodium hydroxide; In methanol; dichloromethane; water;

DOI:10.1016/j.ejmech.2017.05.029

upstream raw materials:

methanol

diazomethane

4-carboxymethyl-5-ethylidene-6-(3,4,5-trihydroxy-6-hydroxymethyl-tetrahydropyran-2-yloxy)-5,6-dihydro-4H-pyran-3-carboxylic acid methyl ester

oleuropeine

Downstream raw materials:

D-Glucose

p-hydroxyphenethyl alcohol

Refernces

• 1、 Samara, Pinelopi,Christoforidou, Nikoleta,Lemus, Christelle,Argyropoulou, Aikaterini,Ioannou, Kyriaki,Vougogiannopoulou, Konstantina,Aligiannis, Nektarios,Paronis, Efthimios,Gaboriaud-Kolar, Nicolas,Tsitsilonis, Ourania,Skaltsounis, Alexios-Leandros. "New semi-synthetic analogs of oleuropein show improved anticancer activity in?vitro and in?vivo". . p. 11 - 29. Retrieved 2017/05/29.