ArticleThe Journal of organic chemistry2014
Synthesis and reactivity of 4'-deoxypentenosyl disaccharides.
Article in The Journal of organic chemistry, 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 5 papers.
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Who cites it
5 citing papers in PubMed.
- Creating glycoside diversity through stereoselective carboboration of glycals.Nature communications · 2024Article
- Complement receptor 3-dependent engagement byOpen biology · 2024Article
- Modulating Heparanase Activity: Tuning Sulfation Pattern and Glycosidic Linkage of Oligosaccharides.Journal of medicinal chemistry · 2020Article
- A minimalist approach to stereoselective glycosylation with unprotected donors.Nature communications · 2017Article
- Mechanistic Investigations into the Application of Sulfoxides in Carbohydrate Synthesis.Chemistry (Weinheim an der Bergstrasse, Germany) · 2016Review
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6 authors.
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Abstract
4-Deoxypentenosides (4-DPs) are versatile synthons for rare or higher-order pyranosides, and they provide an entry for structural diversification at the C5 position. Previous studies have shown that 4-DPs undergo stereocontrolled DMDO oxidation; subsequent epoxide ring-openings with various nucleophiles can proceed with both anti or syn selectivity. Here, we report the synthesis of α- and β-linked 4'-deoxypentenosyl (4'-DP) disaccharides, and we investigate their post-glycosylational C5' additions using the DMDO oxidation/ring-opening sequence. The α-linked 4'-DP disaccharides were synthesized by coupling thiophenyl 4-DP donors with glycosyl acceptors using BSP/Tf2O activation, whereas β-linked 4'-DP disaccharides were generated by the decarboxylative elimination of glucuronyl disaccharides under microwave conditions. Both α- and β-linked 4'-DP disaccharides could be epoxidized with high stereoselectivity using DMDO. In some cases, the α-epoxypentenosides could be successfully converted into terminal l-iduronic acids via the syn addition of 2-furylzinc bromide. These studies support a novel approach to oligosaccharide synthesis, in which the stereochemical configuration of the terminal 4'-DP unit is established at a post-glycosylative stage.
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