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Synthesis of a useful lauryl thioglycoside of sialic acid and its application |
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| Authors: | Koji Matsuoka Tomotsune Onaga Jun-Ichi Sakamoto Nobuo Sakairi Daiyo Terunuma |
| Institution: | a Department of Functional Materials Science, Faculty of Engineering, Saitama University, Saitama 338-8570, Japan b Japan Association for the Advancement of Medical Equipment, Hongo, Bunkyo 133-0033, Japan c Division of Bioscience, Graduate School of Environmental Earth Science, Hokkaido University, Sapporo 060-0810, Japan |
| 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 Lauryl mercaptan Sialic acid Glycosidation Carbohydrates |
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