ABSTRACT
Synthesis of sulfides proceeding from neomenthanethiol and diacetone- galacto-, diacetonefructopyranose, monoacetoneglucofUranose with yields up to 98% was carried out. Under oxidation of sulfides with diacetone-protected carbohydrate moieties, new diastereomeric sulfoxides were synthesized. As oxidants, m-C’PBA, CHP/VO(acac)2, and TBHP/ VO(acac)2 systems were used. Based on 6-thiodiacetonegalactopyranose, 1-thiodiacetonefructopyranose, and terpenic thiols: neomentanethiol, isobornanethiol, tra«s-verbenethiol, myrthenethiol, and cN-myrtanethiol both symmetrical disulfides with terpene and carbohydrate moieties of up to 41% and 13%, respectively, and asymmetrical disulfides containing simultaneously terpene and monosaccharide fragments in an amount of 51-90% by weight of the reaction products were prepared. To increase the water solubility of sulfides and sulfoxides obtained, the removal of the isopropylidene protection was performed. The estimation of membrane- protective and antioxidant properties of thioglycosides with monoterpene and monosaccharide fragments on the basis of their ability to inhibit H2O2-induced hemolysis of erythrocytes and to break the accumulation of secondary products of lipid peroxidation (LPO) was carried out.
