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

Journal of the American Chemical Society, Год журнала: 2024, Номер 146(47), С. 32269 - 32275

Опубликована: Ноя. 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.

Язык: Английский

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Highly Stereoselective Synthesis of Bis-C-ferrocenyl Glycosides via Palladium-Catalyzed Directed C–H Glycosylation

Organic Letters, Год журнала: 2023, Номер 25(22), С. 4070 - 4074

Опубликована: Май 26, 2023

Conjugation of carbohydrates to ferrocene scaffolds is great value in drug design, given the nontoxic and lipophilic nature ferrocene. However, efficient stereoselective synthesis C-ferrocenyl glycosides remains a challenge. Herein, we developed Pd-catalyzed C-H glycosylation provide rapid access sole bis-C-ferrocenyl good high yields (up 98% yield) with exclusive stereoselectivity. A diverse range glycosyl chlorides were well tolerated, including d-mannose, d-glucose, l-xylose, l-rhamnose, d-mannofuranose, d-ribofuranose. Additionally, mononuclear PdII intermediate was characterized by X-ray single-crystal diffraction, might participate palladation step.

Язык: Английский

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Synthesis of heteroaryl C-glycosides via Ru-catalyzed C–H activation/cyclization: dioxazolone glycogen designs and applications

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(13), С. 3609 - 3613

Опубликована: Янв. 1, 2024

New glycogen reagents of dioxazolone anomers have been developed. The versatile heteroarene C -glycosides synthesized using a Ru-catalyzed C–H activation/annulation strategy, employing these anomers.

Язык: Английский

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

Science China Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Янв. 2, 2025

Язык: Английский

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Ruthenium-Catalyzed Remote Trifunctionalization of Non-Activated Alkenes via Cyano Migration and meta-C(sp²)–H Functionalization

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Янв. 28, 2025

A novel Ru-catalyzed radical-triggered trifunctionalization of hexenenitriles is presented, employing a strategy remote cyano group migration and meta-C(sp2)-H functionalization. Through migration, the alkenyl moiety undergoes difunctionalization to formation benzylic radical intermediate. This intermediate facilitates para-selective C-H bond addition relative C-Ru within Ru(III) complex, ultimately enabling trifunctionalization. methodology provides an efficient route diverse array nitrile-containing compounds with broad functional compatibility.

Язык: 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, Год журнала: 2025, Номер unknown

Опубликована: Апрель 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.

Язык: Английский

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Synthesis, Antimicrobial, and Anticancer Activity of Novel Sugar Hydrazones and Schiff Bases Linked to C-Furyl Glycosides

Russian Journal of General Chemistry, Год журнала: 2025, Номер 95(4), С. 873 - 883

Опубликована: Апрель 1, 2025

Язык: Английский

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Stereoselective synthesis of C-glycosides from glycals and organotrifluoroborate salts

Chemical Communications, Год журнала: 2025, Номер unknown

Опубликована: Янв. 1, 2025

Harnessing aryltrifluoroborates' stability and reactivity, we developed a Pd-catalyzed stereoselective C-glycosylation under ambient conditions, yielding diverse C-aryl glycosides with exclusive α-stereoselectivity compatibility hydroxyl, amide, amine groups. This method enables functionalization to produce unprotected C-pyranosides, 2,3-dideoxy 2,3-epoxy sugars, late-stage of natural products drugs.

Язык: Английский

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Ru(II)‐Catalyzed C‐H Alkylation of Indoles at the C‐3 Position with Coumarin‐3‐Carboxylic Acids

ChemistrySelect, Год журнала: 2025, Номер 10(20)

Опубликована: Май 1, 2025

Abstract A ruthenium(II)‐catalyzed C3‐selective C─H activation of indoles bearing a pyridyl or pyrimidine directing group and subsequent conjugated/decarboxylative addition to coumarin‐3‐carboxylic acids has been demonstrated. This protocol efficiently afforded variety coumarin‐containing with excellent site selectivity, satisfactory product yields, functional tolerance.

Язык: Английский

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Photoinduced Ruthenium-Catalyzed meta-C–H Glycosylation

ACS Catalysis, Год журнала: 2025, Номер unknown, С. 10542 - 10549

Опубликована: Июнь 5, 2025

Язык: Английский

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