A novel O-fucosylation strategy preactivated by (p-Tol)2SO/Tf2O and its application for the synthesis of Lewis blood group antigen Lewisa |
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| Authors: | Cui-yun Li Guang-jian Liu Wei Du Yuan Zhang Guo-wen Xing |
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| Affiliation: | 1. College of Chemistry, Beijing Normal University, Beijing 100875, China;2. Key Laboratory of Theoretical and Computational Photochemistry, Ministry of Education, College of Chemistry, Beijing Normal University, Beijing 100875, China |
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| Abstract: | Based on a preactivation strategy using (p-Tol)2SO/Tf2O, a new O-fucosylation method with thioglycoside as donor under mild conditions was reported. High yields and excellent α-stereoselectivities of the fucosylation were obtained with secondary sugar alcohol as acceptors. Moreover, the novel fucosylation strategy was successfully applied to the synthesis of an important Lewis blood group antigen Lewisa, which was obtained in nine linear steps with 27% overall yield. |
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| Keywords: | Fucosylation Glycosylation Preactivation Corresponding author. |
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