Mazur, Marcelina published the artcile4′-Methoxyphenacyl-Assisted Synthesis of β-Kdo Glycosides, COA of Formula: C13H19NO3, the main research area is Kdo glycoside stereoselective synthesis anomeric methoxyphenacyl auxiliary group thioglycoside.
3-Deoxy-β-D-manno-oct-2-ulosonic acid (β-Kdo) glycosides are mainly found in capsular polysaccharides and extracellular exopolysaccharides from Gram-neg. bacteria. These compounds have profound biol. implications in immune response and act as virulence factors. We have developed a novel methodol. for the stereoselective synthesis of β-Kdo glycosides via the use of a 4′-methoxyphenacyl (Phen) auxiliary group at the C1 position of a peracetylated β-Kdo thioglycoside. Under the promotion of NIS/AgOTf in acetonitrile, a series of Kdo glycosides was synthesized in good yield and β-selectivity while minimizing the formation of undesirable glycals. Stereoselectivity of the glycosylation was shown to be modulated by various factors such as promotor, solvent, anomeric ratio of donor, nature of acceptor, and Phen substitution. Chemoselective cleavage of the Phen group was performed under the action of Zn/HOAc. DFT calculations together with exptl. results suggested that α-triflate and a six-membered α-spiroPhen are plausible intermediates of the reaction, accounting for the enhanced formation of β-Kdo glycosides. The developed methodol. could be applied to the synthesis of β-Kdo-containing glycans from pathogenic bacteria.
Journal of Organic Chemistry published new progress about Exopolysaccharides Role: NPO (Natural Product Occurrence), BIOL (Biological Study), OCCU (Occurrence) (extracellular). 87905-98-4 belongs to class alcohols-buliding-blocks, name is Benzyl (5-hydroxypentyl)carbamate, and the molecular formula is C13H19NO3, COA of Formula: C13H19NO3.
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