Synthesis of glycosyl phosphates from 1,2-orthoesters and application to in situ glycosylation reactions

Organic Letters
Alessandra RavidàPeter H Seeberger

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.

References

Jul 12, 1988·Biochemistry·F MichonH J Jennings
Jan 1, 1994·Advances in Carbohydrate Chemistry and Biochemistry·R R Schmidt, W Kinzy
Jan 1, 1997·Advances in Carbohydrate Chemistry and Biochemistry·P J Garegg
Jul 13, 2000·Organic Letters·B A Garcia, D Y Gin
Jul 25, 2000·Organic Letters·O J PlanteP H Seeberger
Feb 27, 2001·Science·O J PlanteP H Seeberger
Sep 27, 2001·Journal of the American Chemical Society·O J PlanteP H Seeberger
Jun 5, 2003·Chemical Communications : Chem Comm·Peter H Seeberger

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Citations

May 2, 2008·Organic Letters·Laurel K Mydock, Alexei V Demchenko
Jan 29, 2009·Angewandte Chemie·Xiangming Zhu, Richard R Schmidt
Apr 29, 2015·Chembiochem : a European Journal of Chemical Biology·Shinya HanashimaYoshiki Yamaguchi
Dec 4, 2008·Journal of the American Chemical Society·Siwarutt BoonyarattanakalinPeter H Seeberger
Aug 1, 2012·Organic Letters·Landon John G EdgarMark Nitz
Dec 7, 2011·The Journal of Organic Chemistry·Clara UrielBert Fraser-Reid
May 18, 2019·The Journal of Organic Chemistry·Nithinan SawettanaiSiwarutt Boonyarattanakalin
Jun 29, 2018·Chemical Reviews·Matteo PanzaAlexei V Demchenko
Jul 25, 2013·Journal of the American Chemical Society·Gloria J ShengLinda C Hsieh-Wilson

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