Emerging Advances of the Radical Pathway Glycosylation Enabled by Bench‐Stable Glycosyl Donors: Glycosyl Sulfoxides, Glycosyl Sulfones, and Glycosyl Sulfinates

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(19), P. 4017 - 4041

Published: July 30, 2024

Abstract In synthetic carbohydrate chemistry, the modification of glycosyl radicals pathway stands as a central area focus. The radical‐based reactions often demonstrate remarkable compatibility with various functional groups owing to mild initiation conditions. particular, identification novel radical precursors, combined advanced reaction techniques, has substantially broadened scope compound synthesis. Despite presence versatile donors, synthesis noble donors is still addressed need and challenges associated sugar chemistry. Currently, new class precursors been developed which enables production C ‐, S O N ‐glycosides efficiently. this light, we highlight strategies towards bench‐stable sulfoxides, sulphone, sulfite that can enable site‐, regio‐ stereoselective transformation protected or naked synthons in Here, review article covers recent developments selective diversification such alkylation, arylation, alkenylation, sulfuration, C−H activation, DNA conjugation via along mechanistic aspects, challenges, future directions.

Language: Английский

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Synthesis of C-Alkyl Glycosides from Alkyl Bromides and Glycosyl Carboxylic Acids via Ni/Photoredox Dual Catalysis

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(16), P. 11136 - 11147

Published: Aug. 6, 2024

-Alkyl glycosides, an important class of C-glycosides, are widely found in various drugs and natural products. The synthesis

Language: Английский

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C–OH Bond Activation for Stereoselective Radical C-Glycosylation of Native Saccharides

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(47), P. 32269 - 32275

Published: Nov. 15, 2024

Radical C-glycosylation presents a flexible and efficient method for synthesizing C-glycosides. Existing methods always require multistep processes generating anomeric radicals. In this study, we introduce streamlined approach to produce radicals through direct C-OH bond homolysis of unmodified saccharides, eliminating the need protection, deprotection, or activation steps. These selectively couple with activated alkenes, yielding products high stereoselectivity (>20:1). This is applicable variety native monosaccharides, such as l-arabinose, d-arabinose, d-xylose, l-xylose, d-galactose, β-d-glucose, α-d-glucose, l-ribose, well oligosaccharides including α-lactose, d-(+)-melibiose, acarbose. We also extend amino acid peptide derivatives, demonstrate synthesis an anti-inflammatory agent.

Language: Английский

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Modular assembly of complex C-alkyl glycoside enabled via cooperative NHC and photoredox catalysis

Science China Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 2, 2025

Language: Английский

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Cobalt-Catalyzed Cross-Coupling of Glycosyl Sulfones with Zinc reagents toward the Stereoselective Synthesis of C(sp/sp²)-Glycosides

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: April 18, 2025

A cobalt-catalyzed desulfonylative cross-coupling of glycosyl sulfones with organozinc reagents toward the stereoselective synthesis C-glycosides is reported. The new C-glycoside proceeds under mild reaction conditions and exhibits tolerance to a range functional groups. Diverse alkynylated, arylated, alkenylated products are formed high efficiency excellent diastereoselectivity. Mechanistic studies indicate radical pathway.

Language: Английский

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