Stereoselective gem-C,B-Glycosylation via 1,2-Boronate Migration

Journal of the American Chemical Society, Journal Year: 2022, Volume and Issue: 144(6), P. 2460 - 2467

Published: Feb. 3, 2022

A novel protocol is established for the long-standing challenge of stereoselective geminal bisglycosylations saccharides. The merger PPh3 as a traceless glycosidic leaving group and 1,2-boronate migration enables simultaneous introduction C–C C–B bonds at anomeric stereogenic center furanoses pyranoses. power this method showcased by set site-selective modifications glycosylation products construction bioactive conjugates skeletons. scarce metal-free 1,1-difunctionalization process alkenes also concomitantly demonstrated.

Language: Английский

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Stabilization of Glucosyl Dioxolenium Ions by “Dual Participation” of the 2,2-Dimethyl-2-(ortho-nitrophenyl)acetyl (DMNPA) Protection Group for 1,2-cis-Glucosylation

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(14), P. 9139 - 9147

Published: June 24, 2022

The stereoselective introduction of glycosidic bonds is paramount importance to oligosaccharide synthesis. Among the various chemical strategies steer stereoselectivity, participation by either neighboring or distal acyl groups used particularly often. Recently, use 2,2-dimethyl-2-(ortho-nitrophenyl)acetyl (DMNPA) protection group was shown offer enhanced steering compared other groups. Here, we investigate origin stereoselectivity induced DMNPA through systematic glycosylation reactions and infrared ion spectroscopy (IRIS) combined with techniques such as isotopic labeling anomeric center isomer population analysis. Our study indicates that does not lie in direct nitro moiety but formation a dioxolenium strongly stabilized group.

Language: Английский

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Highly Stereoselective Assembly of 1,2-cis-Arap Linkages

Organic Letters, Journal Year: 2023, Volume and Issue: 25(16), P. 2788 - 2792

Published: April 14, 2023

Highly stereoselective construction of 1,2-cis-Arap linkages has been achieved, which featured a broad range alcoholic acceptors, including strong nucleophiles and complex bioactive molecules. This method was applied to regioselective orthogonal one-pot synthesis pentasaccharide, the structural motif side chain in type II arabinogalactan.

Language: Английский

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Recent chemical synthesis of plant polysaccharides

Current Opinion in Chemical Biology, Journal Year: 2023, Volume and Issue: 77, P. 102387 - 102387

Published: Sept. 15, 2023

Language: Английский

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Chemical Synthesis of Complex Carbohydrates

Handbook of experimental pharmacology, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

Language: Английский

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