期刊名称：Proceedings of the National Academy of Sciences
印刷版ISSN：0027-8424
电子版ISSN：1091-6490
出版年度：2003
卷号：100
期号：3
页码：797-802
DOI：10.1073/pnas.0337590100
语种：English
出版社：The National Academy of Sciences of the United States of America
摘要：The total synthesis of the sialic acid-containing antigenic epitope fucose GM1 (Fuc-GM1) by an improved reactivity-based one-pot synthetic strategy is reported. Based on a thioglycoside reactivity database, three saccharide building blocks, 3, 4, and 5, were designed and prepared to incorporate a descending order of reactivity toward thiophilic activation. Using the reactivity-based one-pot synthetic method, the fully protected Fuc-GM1 glycoside 2 was furnished in a facile manner, which was globally deprotected to give the Fuc-GM1 glycoside 1. In addition, using the promoter system 1-(benzensulfinyl)piperidine/trifluoromethanesulfonic anhydride, the product yield was improved and the reaction time was reduced in comparison with the N-iodosuccinimide/trifluoromethanesulfonic acid- and dimethyl (thiomethyl) sulfonium trifluoromethanesulfonate-promoted systems.
