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TitleTotal synthesis of LewisX using a late-stage crystalline intermediate
Publication TypeJournal Article
Year of Publication2015
AuthorsMunneke, S., Painter G.F., Gainsford G.J., Stocker B.L., and Timmer M.S.M.
JournalCarbohydrate Research
Pagination1 - 7
Date Published2015
ISSN00086215 (ISSN)
Keywordsarticle, blood group Lewis system, carbohydrate analysis, carbohydrate synthesis, Carbohydrates, carbon nuclear magnetic resonance, chemical structure, Convergent synthesis, Crystalline materials, Efficient synthesis, Esterification, Fucosylation, galactose, glycosylation, Linear sequence, one pot synthesis, priority journal, Protecting group, proton nuclear magnetic resonance, Regio-selective, Regioselectivity, sialyl Lewis x antigen, Synthesis (chemical), thioglycoside, Thioglycosides, Total synthesis, trisaccharide
AbstractAbstract Herein, we report on a highly efficient synthesis of a crystalline protected LewisX trisaccharide that was converted to LewisX following global deprotection. The trisaccharide was prepared in a highly convergent synthesis (seven steps, longest linear sequence) and in a 38% overall yield using a strategy that involved the regioselective glycosylation of a GlcNAc acceptor with a galactose thioglycoside donor, followed by fucosylation of the remaining free GlcNAc hydroxyl as key steps. The core trisaccharide also has the potential to be converted to other members of the Type-2 Lewis family of antigens due to the orthogonal nature of the protecting groups employed. © 2015 Published by Elsevier Ltd.

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