Synthetic studies toward the anthrax tetrasaccharide: alternative synthesis of this antigen

Carbohydrate Research
Ophélie MilhommeCyrille Grandjean

Abstract

The synthesis of the anthrax tetrasaccharide, amenable for conjugation, has been envisaged by both [2+2] and [1+3] approaches from D-fucose and L-rhamnose. The successful route reported herein relies on a [1+3] strategy in which the 1,2-trans-glycosidic linkages have been secured using a participating group at the 2-position of the donors using conventional thio as well as trichloroacetimidate glycosylation chemistry. The exchange of the ester to benzyl protective groups on the rhamnosyl moiety was key to achieve the final assembly and functionalization of the tetrasaccharide.

References

Sep 5, 2009·Molecular Aspects of Medicine·Robert J CybulskiAlison D O'Brien
Oct 2, 2009·Clinical and Vaccine Immunology : CVI·Andrea KuehnRoland Grunow
Jan 28, 2010·Journal of Medicinal Chemistry·Dimitrios G Bouzianas

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Citations

Feb 28, 2016·The Journal of Biological Chemistry·Emmanuel MaesYann Guerardel
Aug 22, 2018·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Riccardo De RiccoRoberto Adamo
Sep 27, 2012·Organic & Biomolecular Chemistry·Ophélie MilhommeCyrille Grandjean

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