ChemicalBook CAS DataBase List Oleoside

Oleoside synthesis

5synthesis methods

Product Name:Oleoside
CAS Number:178600-68-5
Molecular formula:C16H22O11
Molecular Weight:390.34

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Yield: 90%

Reaction Conditions:

with sodium hydroxide in water at 100;Microwave irradiation;

Steps:

4.4.1. Synthesis of oleoside-11-methylester 2 and oleoside 3
General procedure: Oleuropein 1 (1g, 1.85mmol) was dissolved in 50mL of 1N NaOH solution. The mixture was subjected to microwave radiation and the reaction monitored with TLC. After completion (around 10min), a 1N HCl solution was added to reach a pH around 4-5. After removal of the solvent under vacuum, the crude mixture was subjected to column chromatography (CH₂Cl₂:MeOH 95/5 to 50/50). Overall, 324.5mg of 2 were collected (68% yield). The analytical data of 2 were conform to the literature.

References:

Samara, Pinelopi;Christoforidou, Nikoleta;Lemus, Christelle;Argyropoulou, Aikaterini;Ioannou, Kyriaki;Vougogiannopoulou, Konstantina;Aligiannis, Nektarios;Paronis, Efthimios;Gaboriaud-Kolar, Nicolas;Tsitsilonis, Ourania;Skaltsounis, Alexios-Leandros [European Journal of Medicinal Chemistry,2017,vol. 137,p. 11 - 29]