title: Synthesis of glycosyl phosphates from 1,2-orthoesters and application to in situ glycosylation reactions.
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.
authors.affiliation: Laboratorium für Organische Chemie, Swiss Federal Institute of Technology, ETH Zürich, HCI F315, Wolfgang-Pauli Strasse 10, 8093 Zürich, Switzerland.
authors.forename: Alessandra
authors.initials: A
authors.lastname: Ravidà
authors.forename: Xinyu
authors.initials: X
authors.lastname: Liu
authors.forename: Linda
authors.initials: L
authors.lastname: Kovacs
authors.forename: Peter H
authors.initials: PH
authors.lastname: Seeberger
mesh_terms: D000939:Epitopes / Q000187:drug effects* / Q000235:genetics; D006027:Glycosides / Q000737:chemistry*; D006031:Glycosylation; D015394:Molecular Structure; D013291:Streptococcus / Q000187:drug effects* / Q000235:genetics; D013403:Sugar Phosphates / Q000138:chemical synthesis*
chemical_list: D000939:Epitopes; D006027:Glycosides; D013403:Sugar Phosphates