Author/Authors :
Matsuoka، نويسنده , , Koji and Onaga، نويسنده , , Tomotsune and Mori، نويسنده , , Tomonori and Sakamoto، نويسنده , , Jun-ichi and Koyama، نويسنده , , Tetsuo and Sakairi، نويسنده , , Nobuo and Hatano، نويسنده , , Ken and Terunuma، نويسنده , , Daiyo، نويسنده ,
Abstract :
An efficient synthesis of a useful thioglycosyl donor 2 was accomplished directly from known peracetylated sialic acid methyl ester and 1-dodecanethiol (lauryl mercaptan) in the presence of BF3–OEt2. The reactivities of the lauryl glycosides for glycosidation by means of TMSOTf as a convenient promoter were investigated, and the lauryl thioglycoside showed satisfactory activities. Further transformation of the lauryl glycoside was also attempted to give a 5-azide analogue 14 of the sialic acid, which was also reacted with a secondary alcohol in the presence of TMSOTf to give known glycoside 15 in high yield.
Keywords :
Thioglycosides , Sialic acid , carbohydrates , Glycosidation , Lauryl mercaptan
