☆ 4.8 Article

Chemical Glycosylation with p-Methoxyphenyl (PMP) Glycosides via Oxidative Activation

ORGANIC LETTERS (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, Multidisciplinary

ortho-Methoxycarbonylethynylphenyl Thioglycosides (MCEPTs): Versatile Glycosyl Donors Enabled by Electron-Withdrawing Substituents and Catalyzed by Gold(I) or Cu(II) Complexes

Hui Liu et al.

Summary: With easily accessible and operator-friendly reagents, shelf-stable ortho-methoxycarbonylethynylphenyl thioglycosides were efficiently prepared. A novel glycosylation protocol utilizing Au(I) or Cu(II) complexes was established, allowing for expanded substrate scope and versatility in glycoside synthesis. The mechanism and side product formation of C-glycosylation were also investigated.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2023)

添加到收藏夹

Article Chemistry, Organic

K2S2O8-Induced [4+2] Annulation of Tertiary Anilines and Alkenes toward Tetrahydroquinolines

Jianguo Hu et al.

Summary: We report a protocol for constructing tetrahydroquinolines from bulk chemicals (alkenes and anilines) induced by K2S2O8. The method exhibits operational simplicity, wide scope, mild conditions, and a transition-metal-free system.

ORGANIC LETTERS (2023)

添加到收藏夹

Article Chemistry, Multidisciplinary

CuII-mediated DNA base pairing of a triazole-4-carboxylate nucleoside prepared by click chemistry

Lingyun Hu et al.

Summary: Artificial metal-mediated DNA base pairing is a promising strategy for creating highly functionalized DNA supramolecules. A novel ligand-type triazole-4-carboxylate (Taz(C)) nucleoside was developed through the click reaction. Taz(C) nucleosides were found to form a stable Taz(C)-Cu-II-Taz(C) base pair inside DNA duplexes, leading to Cu-II-specific duplex stabilization (ΔTm = +7.7 °C). This study demonstrates the usefulness of triazole derivatives in the development of metal-mediated base pairing.

CHEMICAL COMMUNICATIONS (2023)

添加到收藏夹

Article Chemistry, Multidisciplinary

Hydrogen bond activated glycosylation under mild conditions

Ke Xiao et al.

Summary: The new glycosylation system utilizes a charged thiourea hydrogen-bond-donor catalyst and PTFAI donors, showing broad substrate scope, stereoselectivity, and good yields. The mild catalysis conditions make it suitable for synthesizing challenging phenolic glycosides and a chemoselective glycosylation procedure.

CHEMICAL SCIENCE (2022)

添加到收藏夹

Article Chemistry, Organic

GeCl2•Dioxane-AgBF4 Catalyzed Activation of Glycosyl Fluorides for Glycosylation

Qiuyu Zhu et al.

Summary: A catalytic glycosyl fluoride activation system using the GeCl2·dioxane-AgBF4 combination was developed, involving reversible activation of C-F bond and reversible chloride ion transfer. This system is easy to operate, proceeds at room temperature, and has a broad scope of substrates.

ORGANIC LETTERS (2022)

添加到收藏夹

Article Chemistry, Organic

Insights into the Activation of Alkyne-Installed Glycosyl Donors with Dual Acidic Metal Catalysts: Reaction Pathway, Influencing Factors, and Enlightenment for Glycosylation

Chenglin Cai et al.

Summary: The activation modes of alkyne-installed glycosyl donors with dual acidic metal catalysts depend on the nature of the catalysts, protecting groups on sugar rings, type of sugars, and structure of aglycones. The acidity-promoted reaction mode offers higher efficiency and yields in glycosylation reactions.

ORGANIC LETTERS (2022)

添加到收藏夹

Review Chemistry, Multidisciplinary

Cu(I)-Catalyzed Click Chemistry in Glycoscience and Their Diverse Applications

Anand K. Agrahari et al.

Summary: The review discusses the successful utilization of CuAAC or click chemistry in the field of glycoscience, focusing on the synthesis of triazole-appended carbohydrate-containing molecular structures such as glycohybrids, glycoconjugates, glycopolymers, glycopeptides, glycoproteins, glycolipids, glycoclusters, and glycodendrimers through regioselective triazole forming modular and bio-orthogonal coupling protocols. These glycoproducts find widespread applications as enzyme inhibitors in drug discovery and development, sensing, gelation, chelation, glycosylation, and catalysis. Additionally, the review provides insights into the impact of click chemistry and outlines future perspectives in various emerging disciplines of science and technology.

CHEMICAL REVIEWS (2021)

添加到收藏夹

Article Chemistry, Multidisciplinary

Visible-light-promoted 3,5-dimethoxyphenyl glycoside activation and glycosylation

Yafei Cao et al.

Summary: A new glycosylation method using visible light and 3,5-dimethoxyphenyl glycoside as the donor was developed, which delivers O-glycosides and N-glycosides in moderate to excellent yields with a wide range of O-nucleophiles and nucleobases as the glycosyl acceptors.

CHEMICAL COMMUNICATIONS (2021)

添加到收藏夹

Article Multidisciplinary Sciences

Bioorthogonal chemistry

Samuel L. Scinto et al.

Summary: Bioorthogonal chemistry involves high-yielding chemical reactions in biological environments that are rapid and selective, playing essential roles in various fields such as biomedical imaging and drug delivery. Its applications are diverse and include genetic code expansion, drug target identification, and antibody-drug conjugation.

NATURE REVIEWS METHODS PRIMERS (2021)

添加到收藏夹

Article Chemistry, Multidisciplinary

Metal-free approach for hindered amide-bond formation with hypervalent iodine(III) reagents: application to hindered peptide synthesis

Hyo-Jun Lee et al.

Summary: A new bio-inspired approach for amide and peptide synthesis using a-amino esters with a potential activating group (PAG) at the ester residue is reported. The ester functionality is activated under mild metal-free conditions by exploiting the dearomatization of phenols with hypervalent iodine(III) reagents. Highly reactive acyl fluoride intermediates are successfully generated using a pyridine hydrogen fluoride complex, facilitating the smooth formation of sterically hindered amides and peptides from bulky amines and a-amino esters.

GREEN CHEMISTRY (2021)

添加到收藏夹

Review Engineering, Environmental

Persulfate-Based Advanced Oxidation: Critical Assessment of Opportunities and Roadblocks

Jaesang Lee et al.

ENVIRONMENTAL SCIENCE & TECHNOLOGY (2020)

添加到收藏夹

Article Chemistry, Multidisciplinary

Catalytic and Atom-Economic Glycosylation using Glycosyl Formates and Cheap Metal Salts

Liang Yang et al.

CHEMSUSCHEM (2020)

添加到收藏夹

Article Chemistry, Organic

Cholesteryl 6-O-acyl-α-glucosides from diverseHelicobacterspp. signal through the C-type lectin receptor Mincle

Dylan G. M. Smith et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2020)

添加到收藏夹

Article Biology

Cholesteryl α-D-glucoside 6-acyltransferase enhances the adhesion of Helicobacter pylori to gastric epithelium

Hau-Ming Jan et al.

COMMUNICATIONS BIOLOGY (2020)

添加到收藏夹

Article Chemistry, Multidisciplinary

Glycosylation with 3,5-Dimethyl-4-(2′-phenylethynylphenyl)phenyl (EPP) Glycosides via a Dearomative Activation Mechanism

Zhifei Hu et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2019)

添加到收藏夹

Article Chemistry, Organic

Visible-Light-Mediated, Chemo- and Stereoselective Radical Process for the Synthesis of C-Glycoamino Acids

Peng Ji et al.

ORGANIC LETTERS (2019)

添加到收藏夹

Review Chemistry, Multidisciplinary

Catalytic Glycosylations in Oligosaccharide Synthesis

Michael Martin Nielsen et al.

CHEMICAL REVIEWS (2018)

添加到收藏夹

Review Chemistry, Multidisciplinary

One-Pot Protection, Glycosylation, and Protection-Glycosylation Strategies of Carbohydrates

Suvarn S. Kulkarni et al.

CHEMICAL REVIEWS (2018)

添加到收藏夹

Article Chemistry, Multidisciplinary

An Empirical Understanding of the Glycosylation Reaction

Sourav Chatterjee et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2018)

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, Multidisciplinary

Cu-Catalyzed Click Reaction in Carbohydrate Chemistry

Vinod K. Tiwari et al.

CHEMICAL REVIEWS (2016)

添加到收藏夹

Review Chemistry, Multidisciplinary

Chemical O-Glycosylations: An Overview

Rituparna Das et al.

CHEMISTRYOPEN (2016)

添加到收藏夹

Article Chemistry, Organic

Orthogonal cleavage of the 2-naphthylmethyl group in the presence of the p-methoxy phenyl-protected anomeric position and its use in carbohydrate synthesis

Vittorio Cattaneo et al.

ORGANIC CHEMISTRY FRONTIERS (2016)

添加到收藏夹

Article Biochemistry & Molecular Biology

Thioglycosides in Carbohydrate Research

Gaoyan Lian et al.

CARBOHYDRATE RESEARCH (2015)

添加到收藏夹

Review Chemistry, Multidisciplinary

Glycosylated Porphyrins, Phthalocyanines, and Other Porphyrinoids for Diagnostics and Therapeutics

Sunaina Singh et al.

CHEMICAL REVIEWS (2015)

添加到收藏夹

Review Chemistry, Organic

Hafnium Trifluoromethanesulfonate [Hf(OTf)4] as a Unique Lewis Acid in Organic Synthesis

Haruro Ishitani et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2015)

添加到收藏夹

Review Chemistry, Multidisciplinary

Glycomimetics versus Multivalent Glycoconjugates for the Design of High Affinity Lectin Ligands

Samy Cecioni et al.

CHEMICAL REVIEWS (2015)

添加到收藏夹

Article Chemistry, Multidisciplinary

Photocatalytic Synthesis of Dihydrobenzofurans by Oxidative [3+2] Cycloaddition of Phenols

Travis R. Blum et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2014)

添加到收藏夹

Article Chemistry, Organic

Hafnium(IV) Tetratriflate as a Glycosyl Fluoride Activation Reagent

Shino Manabe et al.

JOURNAL OF ORGANIC CHEMISTRY (2013)

添加到收藏夹

Review Chemistry, Multidisciplinary

Mechanism of a Chemical Glycosylation Reaction

David Crich

ACCOUNTS OF CHEMICAL RESEARCH (2010)

添加到收藏夹

Review Chemistry, Multidisciplinary

New Principles for Glycoside-Bond Formation

Xiangming Zhu et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2009)

添加到收藏夹

Review Chemistry, Medicinal

Carbohydrates: A Frontier in Medicinal Chemistry

Pierre Stallforth et al.

JOURNAL OF MEDICINAL CHEMISTRY (2009)

添加到收藏夹

Article Biochemistry & Molecular Biology

Chemical glycobiology: why now?

Peter H. Seeberger

NATURE CHEMICAL BIOLOGY (2009)

添加到收藏夹

Review Biochemistry & Molecular Biology

Covalent inhibitors of glycosidases and their applications in biochemistry and biology

Brian P. Rempel et al.

GLYCOBIOLOGY (2008)

添加到收藏夹

Article Chemistry, Multidisciplinary

Toward fully synthetic glycoproteins by ultimately convergent routes: A solution to a long-standing problem

JD Warren et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2004)

添加到收藏夹

Review Multidisciplinary Sciences

Glycosyl fluoride - A superb glycosyl donor in glycosylation

T Mukaiyama et al.

PROCEEDINGS OF THE JAPAN ACADEMY SERIES B-PHYSICAL AND BIOLOGICAL SCIENCES (2002)

添加到收藏夹

Review Multidisciplinary Sciences

Chemical glycobiology

CR Bertozzi et al.

SCIENCE (2001)

添加到收藏夹

Review Biochemistry & Molecular Biology

Glycosyl fluorides in enzymatic reactions

SJ Williams et al.

CARBOHYDRATE RESEARCH (2000)

添加到收藏夹

© Peeref 2019-2024. All rights reserved.