Oxotriphenylphosphonium salts derived from 3-lup-20(29)-ene-3β,28-diol and method for producing the same

Abstract

Oxotriphenylphosphonium salts of 3-lup-20(29)-ene-3α,28-diol derivatives of general formula 2, where X=-CH(OH), -CH(OAc), =C; Y=-CH2, =C are characterized in that the skeleton of the triterpenoid of general formula 1, where X=-CH(OH), -CH(OAc), =C; Y=-CH2, =C, is connected to the triphenylphosphonium moiety through an oxygen atom. The method for preparing oxotriphenylphosphonium salts of 3-lup-20(29)-ene-3α,28-diol derivatives of general formula 2, where X=-CH(OH), -CH(OAc), =C; Y=-CH2, =C, consists in that the pentacyclic triterpenoid of general formula 1, where X=—CH(OH), -CH(OAc), =C; Y=-CH2, =C, in the amount of 0.20 mmol is contacted in an inert gas environment with triphenylphosphonium tetrafluoroborate in a molar ratio ranging from 0.2:0.44 to 0.2:0.88 in the presence of triphenylphosphine in a molar ratio ranging from 0.2:0.44 to 0.2:0.88 in organic solvents, preferably in dichloromethane in the amount of 6.7 mL to 18 mL of solvent / 0.2 mmol / l, then diisopropyl azodicarboxylate is added dropwise at a temperature of 0°C to 5°C in a molar ratio ranging from 0.2:0.44 to 0.2:0.88, the reaction is carried out at a temperature of 0°C to 5°C for 10 minutes to 60 minutes and at a temperature of 20°C to 35°C for 3 days to 10 days, then the organic solvent is evaporated at a pressure of 20 mmHg to 40 mmHg, preferably 20 mmHg, and the product is purified by column chromatography.