Exploring the Chemistry of Non-sticky Sugars: Synthesis of Polyfluorinated Carbohydrate Analogues of d-Allopyranose |
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Authors: | Vincent Denavit Jacob St-Gelais Thomas Tremblay Prof Denis Giguère |
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Institution: | Département de Chimie, PROTEO, RQRM, Université Laval, 1045 Avenue de la Médecine, Quebec City, QC, G1V 0A6 Canada |
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Abstract: | There is a growing interest in the preparation of polyfluorinated carbohydrates. A limited number of fluorohexopyranosides have been used in biological investigations because of the synthetic challenge they present. Hence, we report the synthesis of fluorinated homodimer, fluorodisaccharides, C-terminal fluoroglycopeptides, lipoic acid fluoroglycoconjugate and trifluoroallopyranoside derivatives functionalized at C-6. Our strategy uses levoglucosan as inexpensive starting material and facilitates an approach to complex carbohydrate analogues with multiple C−F bonds. The challenge of our synthetic route centered around an efficient preparation of crucial 1,6-anhydro-2,4-dideoxy-difluoroglucopyranose and focused on achieving a difficult glycosylation of the trifluoroallopyranose donor. The results clearly highlight challenges related to the preparation of polyhalogenated complex organic molecules and pave the way to access novel medically relevant tools. |
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Keywords: | allopyranose carbohydrates diastereoselectivity fluorodisaccharides fluoroglycopeptides |
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