Synthesis of N-aminoglycoside from the monoethanolamine vinyl ether

Abstract

It is known that the introduction of carbohydrate fragments into the molecules of physiologically active substances not only increases their solubility in water and considerably decreases their toxicity [1–3], but it also makes it possible to transport a drug into the desired part of living organism cells. The modified derivatives of saccharides are of great scientific and practical interest because many of them possess a pronounced broad-spectrum biological activity [4] and are widely used in medicine, for example, as effective antiviral and anticancer preparations [5, 6]. Vinyl ether of monoethanolamine derivatives are used as intermediates in the syntheses of compounds possessing analgesic, psychtropic [7], and radio-protective properties [8]. In [9] synthetic approaches to glycosides based on monoethanolamine were suggested. Optimal conditions for synthesis and isolation of the desired products were shown. However, aminoglycosides based on the monoethanolamine vinyl ether were not reported. In this work we obtained and described a mono-ethanolamine vinyl ether