☆ 4.4 Article

Pd-Catalyzed Stereoselective Synthesis of Nitroalkyl β-C-Glycosides

CHINESE JOURNAL OF ORGANIC CHEMISTRY (2023)

相关参考文献

注意：仅列出部分参考文献，下载原文获取全部文献信息。

Article Chemistry, Organic

Stereoselective Synthesis of 2-Deoxy Glycosides via Iron Catalysis

Mingyu Hou et al.

Summary: An Fe-catalyzed 2-deoxy glycosylation method was developed using 3,4-O-carbonate glycals, providing easy access to alkyl and aryl 2-deoxy glycosides with high yields and exclusive alpha-stereoselectivity. This strategy demonstrated its synthetic utility and advantage through the modification of six natural products and the construction of a tetrasaccharide.

ORGANIC LETTERS (2023)

添加到收藏夹

Article Chemistry, Organic

Stereoselective O-Glycosylation of Glycals with Arylboronic Acids Using Air as the Oxygen Source

Qiuyuan Wang et al.

Summary: An open-air palladium-catalyzed O-glycosylation method using glycals and arylboronic acids has been developed, allowing for the synthesis of various O-glycosides in high yields. Mechanistic studies revealed the origin of the chemo-/stereoselectivity in the reaction.

ORGANIC LETTERS (2022)

添加到收藏夹

Article Chemistry, Organic

TfO-•••H-O-H Interaction-Assisted Generation of a Silicon Cation from Allylsilanes: Access to Phenylallyl Ferrier Glycosides from Glycals

Rupa Bai Addanki et al.

Summary: This study demonstrates the application of strained and bulky protonated TTBPy triflate salt as a mild and efficient organocatalyst in diastereoselective C-Ferrier glycosylation, and reveals the importance of the trapped H2O molecule in the catalyst. The mechanism involves unique anionic triflate and H2O hydrogen-bond interactions that activate allylsilanes, providing unprecedented access to diastereoselective phenylallyl Ferrier glycosides.

ORGANIC LETTERS (2022)

添加到收藏夹

Article Chemistry, Organic

β-C-Glycosylation with 2-Oxindole Acceptors via Palladium- Reactions

Wei-Yi Ding et al.

Summary: This report describes a highly efficient beta-selective C-glycosylation reaction using bicyclic galactals and 2-oxindoles as substrates. The reaction proceeds through a palladium-catalyzed decarboxylative pathway under mild reaction conditions, resulting in high yields. The decarboxylation intermediate of galactal acts as an efficient base to deprotonate the enol tautomer of 2-oxindole, enhancing its nucleophilicity. The beta-selective nucleophilic addition at the anomeric center is due to steric hindrance imposed by the palladium and bulky ligand.

ORGANIC LETTERS (2022)

添加到收藏夹

Article Chemistry, Organic

Palladium catalyzed decarboxylative β-C-glycosylation of glycals with oxazol-5-(4H)-ones as acceptors

Wei-Yi Ding et al.

Summary: Despite the increasing importance of C-glycosides in biochemistry, the strategies for achieving stereoselective C-glycosidic bond formation have received less attention compared to those for O- and N-glycosides. In this study, a beta-C-glycosylation of oxazol-5(4H)-ones, which serve as direct precursors of amino acids, was described. Regardless of the glycal donors and glycosyl acceptors used, the reaction displayed excellent efficiency and chemoselectivity in most cases without the need for exogenous bases. The outstanding stereocontrol at the anomeric center was attributed to the steric hindrance imposed by a bulky phosphine ligand.

ORGANIC CHEMISTRY FRONTIERS (2022)

添加到收藏夹

Article Chemistry, Organic

Open-Air Stereoselective Synthesis of C-Aryl Fucosides/Arabinosides

Lai Mengnan et al.

Summary: An open-air stereoselective preparation of C-aryl fucosides and arabinosides was reported using 3,4-O-carbonate glycals and arylboronic acids. The configurations of products were determined by various analytical techniques. Competitive reactions demonstrated the compatibility of this method and its potential for the preparation of various C-glycosides through functionalization.

CHINESE JOURNAL OF ORGANIC CHEMISTRY (2022)

添加到收藏夹

Article Chemistry, Physical

Catalyst-Controlled Regiodivergent Synthesis of 1-and 3-Thiosugars with High Stereoselectivity and Chemoselectivity

Yuexin Liu et al.

Summary: An effective regiodivergent synthesis of 1- and 3-thiosugars was achieved using palladium and cobalt catalysis, respectively. The difference in the interaction of thiol moieties with Pd and Co catalysis conditions led to the selective formation of beta-1-thiosugars and (3S)-3-thiosugars. Experimental and theoretical calculations supported the proposed mechanism and provided insights into the regioselectivity based on the bond lengths of key intermediates.

ACS CATALYSIS (2021)

添加到收藏夹

Article Chemistry, Organic

Open-Air Stereoselective Construction of C-Aryl Glycosides

Mengnan Lai et al.

ORGANIC LETTERS (2020)

添加到收藏夹

Article Chemistry, Multidisciplinary

Fabrication of Glyco-Metal-Organic Frameworks for Targeted Interventional Photodynamic/Chemotherapy for Hepatocellular Carcinoma through Percutaneous Transperitoneal Puncture

Jun Hu et al.

ADVANCED FUNCTIONAL MATERIALS (2020)

添加到收藏夹

Article Chemistry, Physical

Nitroalkanes as Versatile Nucleophiles for Enzymatic Synthesis of Noncanonical Amino Acids

David K. Romney et al.

ACS CATALYSIS (2019)

添加到收藏夹

Article Oncology

Peptide adjacent to glycosylation sites impacts immunogenicity of glycoconjugate vaccine

Zhongrui Ma et al.

ONCOTARGET (2018)

添加到收藏夹

Review Chemistry, Applied

Synthetic Strategies toward SGLT2 Inhibitors

Anderson R. Aguillon et al.

ORGANIC PROCESS RESEARCH & DEVELOPMENT (2018)

添加到收藏夹

Article Chemistry, Physical

Catalyst-Controlled Stereoselective O-Glycosylation: Pd(0) vs Pd(II)

Hui Yao et al.

ACS CATALYSIS (2017)

添加到收藏夹

Review Chemistry, Multidisciplinary

Recent Advances in the Chemical Synthesis of C-Glycosides

You Yang et al.

CHEMICAL REVIEWS (2017)

添加到收藏夹

Review Chemistry, Organic

Applications of Transition Metal Catalyzed Coupling Reactions in the Synthesis of C-Glycosides

Jinxi Liao et al.

CHINESE JOURNAL OF ORGANIC CHEMISTRY (2017)

添加到收藏夹

Review Pharmacology & Pharmacy

Sodium glucose CoTransporter 2 (SGLT2) inhibitors: Current status and future perspective

Tushar Madaan et al.

EUROPEAN JOURNAL OF PHARMACEUTICAL SCIENCES (2016)

添加到收藏夹

Article Nanoscience & Nanotechnology

Novel Electrochemical Sensing Platform Based on a Molecularly Imprinted Polymer Decorated 3D Nanoporous Nickel Skeleton for Ultrasensitive and Selective Determination of Metronidazole

Yingchun Li et al.

ACS APPLIED MATERIALS & INTERFACES (2015)

添加到收藏夹

Article Infectious Diseases

Metabolism of nitro drugs metronidazole and nitazoxanide in Giardia lamblia: characterization of a novel nitroreductase (GlNR2)

Joachim Mueller et al.

JOURNAL OF ANTIMICROBIAL CHEMOTHERAPY (2013)

添加到收藏夹

Editorial Material Chemistry, Multidisciplinary

The Chemistry-Glycobiology Frontier

Barbara Imperiali

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2012)

添加到收藏夹

Article Chemistry, Medicinal

Potentiating Metronidazole Scaffold against Resistant Trichomonas: Design, Synthesis, Biology and 3D-QSAR Analysis

Lalit Kumar et al.

ACS MEDICINAL CHEMISTRY LETTERS (2012)

添加到收藏夹

Article Chemistry, Organic

Direct C-Glycosylation of Organotrifluoroborates with Glycosyl Fluorides and Its Application to the Total Synthesis of (+)-Varitriol

Jing Zeng et al.

ORGANIC LETTERS (2011)

添加到收藏夹

Article Chemistry, Organic

Synthesis of Mangiferin, Isomangiferin, and Homomangiferin

Zhongtao Wu et al.

JOURNAL OF ORGANIC CHEMISTRY (2010)

添加到收藏夹

Article Chemistry, Organic

Oxidant-Controlled Heck-Type C-Glycosylation of Glycals with Arylboronic Acids: Stereoselective Synthesis of Aryl 2-Deoxy-C-glycosides

De-Cai Xiong et al.

ORGANIC LETTERS (2009)

添加到收藏夹

Article Chemistry, Organic

Expedient synthesis of the α-C-glycoside analogue of the immunostimulant galactosylceramide (KRN7000)

Peter Wipf et al.

ORGANIC LETTERS (2006)

添加到收藏夹

Article Chemistry, Multidisciplinary

The C-glycoside analogue of the immunostimulant alpha-galactosylceramide (KRN7000): Synthesis and striking enhancement of activity

GL Yang et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2004)

添加到收藏夹

Article Chemistry, Organic

Different C-glycosidation products of glucal with alkynyl or propargyl silanes under acidic conditions

M Isobe et al.

ORGANIC LETTERS (2003)

添加到收藏夹

© Peeref 2019-2024. All rights reserved.