Synthesis of a Useful Lauryl Thioglycoside of Sialic Acid and Its Application.

Abstract

The title compound is readily prepared from ester (I) and 1-dodecanethiol and isolated as a mixture of isomers (III) and (VII). Its reactivity with some alcohols under conditions A) is investigated. Generally, the β-isomer (III) gives a higher yield of the products. Furthermore, (III) is transformed to the azide (VIII) which reacts with cyclohexanol to give the known glycoside (IX)/(X). -(MATSUOKA*, K.; ONAGA, T.; MORI, T.; SAKAMOTO, J.-I.; KOYAMA, T.; SAKAIRI, N.; HATANO, K.; TERUNUMA, D.; Tetrahedron Lett. 45 (2004) 51, 9383-9386; Dep. Funct. Mater. Sci. Eng., Fac. Eng., Saitama Univ., Urawa, Saitama 338, Japan; Eng.) -Lindner 15-186

Glyco-silicon Functional Materials as Anti-influenza Virus Agents

“…Therefore, many efforts have been devoted to the development of sialic acid chemistry [19][20]. We have also been synthesizing sialyl oligosaccharides and their glycoclusters by chemical and enzymatic methods, and the glycoclusters have been used in biochemical and biomedical fields [21][22][23][24]. In our ongoing study on the synthesis of sialyl oligosaccharides having thioglycosidic linkages, we have encountered the problem of an inseparable mixture of a desired sialyl derivative and the 2,3-didehydro sialic acid byproduct being obtained in some cases.…”