The Synthesis and Glycoside Formation of Polyfluorinated Carbohydrates

Abstract

Fluorinated carbohydrates have found many applications in the glycosciences. Typically, these contain fluorination at a single position. There are not many applications involving polyfluorinated carbohydrates, here defined as monosaccharides in which more than one carbon has at least one fluorine substituent directly attached to it, with the notable exception of their use as mechanism-9.3.1

Formal Glycosylation of Quinones with exo-Glycals Enabled by Iron-Mediated Oxidative Radical–Polar Crossover

“…The introduction of fluorine, a classic bioisostere of the hydroxyl group, was motivated by the multiple interest of fluorinated glycomimetics as mechanistic probes or drug candidates . In the d -manno series, the α-ketoside product 2f was obtained as a single diastereomer, whereas a complete loss of stereoselectivity was observed from 2-fluoro d -gluco epimer 1e .…”

Synthesis of fluorinated carbocyclic pyrimidine nucleoside analogues

“…23,26 Notwithstanding this, the structural effect of replacing furanose oxygen with CF 2 , both in free nucleosides and nucleotides, and related DNA/RNA sequences is an area primed for exploration. [27][28][29] In line with the achievements highlighted in Figure 1c, we present herein our synthesis of a series of pyrimidine (uridine and cytidine) carbocyclic nucleosides, modified with -monoand di-fluorination at the 6'-position (Figure 2). In addition, we access their ProTide prodrug forms and demonstrate the first examples of diversification to 2'-deoxygentated materials.…”

“…23,26 Notwithstanding this, the structural effect of replacing furanose oxygen with CF 2 , both in free nucleosides and nucleotides, and related DNA/RNA sequences is an area primed for exploration. 27–29…”

Deoxyfluorination tunes the aggregation of cellulose and chitin oligosaccharides and highlights the role of specific hydroxyl groups in the crystallization process

“…In this regard, fluorination of monosaccharides has drawn considerable attention. 26 Fluorination is widely explored in medicinal and material chemistry, [27][28][29][30][31][32][33] owing to the unique features of the F atom. Fluorine is a small, highly electronegative atom that can replace C-OH, C-H, and CvO bonds with the chemically inert C-F bond.…”