Synthesis of glycosyl phosphates from 1,2-orthoesters and application to in situ glycosylation reactions |
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Authors: | Ravidà Alessandra Liu Xinyu Kovacs Linda Seeberger Peter H |
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Institution: | Laboratorium für Organische Chemie, Swiss Federal Institute of Technology, ETH Zürich, HCI F315, Wolfgang-Pauli Strasse 10, 8093 Zürich, Switzerland. |
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Abstract: | reaction: see text] A series of glycosyl phosphates were prepared in high yield by treatment of the corresponding 1,2-orthoesters with dibutyl phosphate. Glycosyl phosphates are efficient glycosylating agents even when used in crude form or when generated in situ. The immunodominant epitope trirhamnoside of group B Streptococcus was prepared to demonstrate the synthetic utility of the method. |
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