Synthesis of glycosyl phosphates from 1,2-orthoesters and application to in situ glycosylation reactions.
[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.
Ravidà
Alessandra
A
Laboratorium für Organische Chemie, Swiss Federal Institute of Technology, ETH Zürich, HCI F315, Wolfgang-Pauli Strasse 10, 8093 Zürich, Switzerland.
Liu
Xinyu
X
Kovacs
Linda
L
Seeberger
Peter H
PH
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*
D000939:Epitopes; D006027:Glycosides; D013403:Sugar Phosphates