Phenanthroline-Assisted Stereoselective Synthesis of 2-Deoxy Glycosides

ACS Omega, Год журнала: 2025, Номер unknown

Опубликована: Апрель 29, 2025

The significance of 2-deoxy glycosides in biologically active compounds is well-established, as they frequently play a pivotal role modulating the efficacy therapeutic agents. sugar embodies distinctive class carbohydrates characterized by marked differences stability, reactivity, and selectivity compared to their counterparts bearing C2-oxygen or other heteroatoms. As result, stereoselective synthesis this carbohydrate complicated its sensitivity acidic conditions propensity for hydrolysis elimination reactions. Furthermore, lack functionality presents an additional challenge controlling stereoselectivity. In study, we report application commercially available phenanthroline effective additive glycosylation aliphatic alcohols phenolic nucleophiles with glycosyl chlorides, facilitating efficient access variety α-2-deoxy high yields synthetically useful Kinetic analyses suggest that plays crucial reaction.

Язык: Английский

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Stereoselective Synthesis of O-Glycosides with Borate Acceptors

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(16), С. 11735 - 11747

Опубликована: Авг. 1, 2023

Borate esters have been applied widely as coupling partners in organic synthesis. However, the direct utilization of borate acceptors O-glycosylation with glycal donors remains underexplored. Herein, we describe a novel resulting formation 2,3-unsaturated O-glycosides and 2-deoxy mediated by palladium copper catalysis, respectively. This method tolerated broad scope trialkyl/triaryl borates various glycals exclusive stereoselectivities high yields. All desired aliphatic/aromatic were generated successfully, without hemiacetal byproducts O→C rearrangement because nature esters. The utility this strategy was demonstrated functionalizing glycoside products to form saturated β-O-glycosides, 2,3-deoxy O-glycosides, 2,3-epoxy O-glycosides.

Язык: Английский

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Origin of site-selectivity of hydrogen atom transfer in carbohydrate C–H alkylations via photoredox catalysis

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(8), С. 2269 - 2276

Опубликована: Янв. 1, 2024

Two major factors, i.e. , C–H σ orbital energy and BDE, account for the HAT site-selectivity of carbohydrates with quinuclidine radical cation.

Язык: Английский

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Glycosyl N-phenyl pentafluorobenzimidates as a new generation of imidate donors for catalytic glycosylation

Chinese Chemical Letters, Год журнала: 2024, Номер unknown, С. 110734 - 110734

Опубликована: Дек. 1, 2024

Язык: Английский

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Highly stereoselective synthesis of α-glycosylated carboxylic acids by phenanthroline catalysis

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(20), С. 5769 - 5783

Опубликована: Янв. 1, 2024

Access to challenging α-glycosylated carboxylic acids in excellent levels of diastereoselectivity was achieved using 2,9-di-butyl-1,10-phenanthroline as an effective catalyst.

Язык: Английский

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A Ligand-Controlled Approach Enabling Gold(I)-Catalyzed Stereoinvertive Glycosylation with Primal Glycosyl ortho-Alkynylbenzoate Donors

Journal of the American Chemical Society, Год журнала: 2024, Номер unknown

Опубликована: Сен. 24, 2024

A diarylurea-containing phosphine ligand-modulated stereoinvertive

Язык: Английский

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Efficient synthesis of novel phenanthroline-dimedone derivatives using Pd@HQBI-SPION as a versatile palladium-immobilized catalyst

Scientific Reports, Год журнала: 2024, Номер 14(1)

Опубликована: Ноя. 1, 2024

This paper presents the synthesis and application of a novel catalyst for carbon-carbon bond formations, comprising palladium immobilized on 2-(5-hydroxyquinolin-8-yl)-1H-benzo[d]imidazole-5-carboxylic acid modified superparamagnetic iron oxide nanoparticles (Pd@HQBI-SPION). The involved attachment HQBI ligands to SPION using APTES, followed by immobilization palladium. Characterization techniques, including FTIR, TEM, magnetic measurements, confirmed successful structural integrity Pd@HQBI-SPION. catalytic activity Pd@HQBI-SPION was evaluated in various formation reactions, demonstrating high efficiency reusability. 8 different derivatives bearing several electron withdrawing donating functionalities were used as starting materials products obtained isolated yields (75-97%). exhibited excellent performance one-pot phenanthroline-dimedone polycyclic via C-alkylation intramolecular O-alkylation phenanthroline with dimedone. are is described. protocol highly selective synthetic method construction aromatic compounds containing nitrogen oxygen atoms.

Язык: Английский

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Urea‐catalyzed N‐Glycosylation of Amides/Azacycles with Glycosyl Halides

Chemistry - An Asian Journal, Год журнала: 2023, Номер 18(23)

Опубликована: Окт. 16, 2023

The efficient synthesis of N-glycosides via direct N-glycosylation amides/azacycles has been reported. glycosylation with glycosyl halides in the presence a catalytic amount urea proceeded smoothly to provide corresponding N-glycosylated amides or nucleosides good excellent yields 1,2-trans-stereoselectivity. Moreover, by addition terpyridine, 1,2-cis-stereoselectivity was achieved.

Язык: Английский

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Base‐Promoted Glycosylation Allows Protecting Group‐Free and Stereoselective O‐Glycosylation of Carboxylic Acids**

Angewandte Chemie, Год журнала: 2023, Номер 135(42)

Опубликована: Авг. 19, 2023

Abstract Here we report a simple and general method to achieve fully unprotected, stereoselective glycosylation of carboxylic acids, employing bench‐stable allyl glycosyl sulfones as donors. Running the reaction under basic conditions was crucial for efficiencies selectivities. Both donor activation stage glycosidic bond forming process are compatible with free hydroxyl groups, thereby allowing use unprotected This transformation is stereoconvergent, occurs mild metal‐free at ambient temperature visible light (455 nm) irradiation, displays remarkable scope respect both partners. Many natural products commercial drugs, including an acid derived from complex anticancer agent taxol, were efficiently glycosylated. Experimental studies provide insights into origin stereochemical outcome.

Язык: Английский

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Organometallic Photocatalyst‐Promoted Synthesis and Modification of Carbohydrates under Photoirradiation

The Chemical Record, Год журнала: 2024, Номер unknown

Опубликована: Дек. 27, 2024

Carbohydrates are natural, renewable, chemical compounds that play crucial roles in biological systems. Thus, efficient and stereoselective glycosylation is an urgent task for the preparation of pure structurally well-defined carbohydrates. Photoredox catalysis has emerged as a powerful tool carbohydrate chemistry, providing alternative addressing some challenges glycochemistry. Over last few decades, Ir- Ru-based organometallic photocatalysts have attracted significant interest because their high stability, high-energy triplet state, strong visible-light absorption, long luminescence lifetime, amenability to ligand modification. This review highlights recent progress photocatalyst-promoted synthesis modification carbohydrates under photoirradiation, well related benefits drawbacks.

Язык: Английский

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