4.4 Article

A mild and efficient synthetic protocol for Ferrier azaglycosylation promoted by ZnCl2/Al2O3

Journal

TETRAHEDRON LETTERS
Volume 51, Issue 23, Pages 3146-3148

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2010.04.045

Keywords

-

Funding

  1. NTU [RG50/08]
  2. Ministry of Education, Singapore [MOE 2009-T2-1-030]

Ask authors/readers for more resources

An improved method for the Ferrier sulfonamidoglycosylation of tri-O-acetyl-D-glucal with different N-nucleophiles has been developed. ZnCl2 impregnated on activated alumina acts as an excellent reagent system for the conversion of 3,4,6-tri-O-acetyl-D-glucal into 2,3-unsaturated-N-pseudoglycals with good yields and preferential alpha-anomeric selectivity. (C) 2010 Elsevier Ltd. All rights reserved.

Authors

I am an author on this paper
Click your name to claim this paper and add it to your profile.

Reviews

Primary Rating

4.4
Not enough ratings

Secondary Ratings

Novelty
-
Significance
-
Scientific rigor
-
Rate this paper

Recommended

Article Chemistry, Analytical

Carbon dots as fluorescent nanoprobe for the determination of N-acetyl-β-D-glucosaminidase activity

Jimei Ma, Heng Zhang, Fangfang Peng, Xiaoqing Yang, Zi-Long Li, Linhao Sun, Hong Jiang

ANALYTICA CHIMICA ACTA (2020)

Article Chemistry, Organic

Unified Strategy toward Stereocontrolled Assembly of Various Glucans Based on Bimodal Glycosyl Donors

Feiqing Ding, Akihiro Ishiwata, Siai Zhou, Xuemei Zhong, Yukishige Ito

JOURNAL OF ORGANIC CHEMISTRY (2020)

Article Biochemistry & Molecular Biology

Lysolipid Chain Length Switches Agonistic to Antagonistic G Protein-Coupled Receptor Modulation

Adam T. Guy, Feiqing Ding, Junpei Abe, Mariko Inoue, Yoshio Hirabayashi, Yukishige Ito, Hiroyuki Kamiguchi, Peter Greimel

ACS CHEMICAL NEUROSCIENCE (2020)

Article Chemistry, Organic

ZnI2-Directed Stereocontrolled α-Glucosylation

Siai Zhou, Xuemei Zhong, Aoxin Guo, Qian Xiao, Jiaming Ao, Wanmeng Zhu, Hui Cai, Akihiro Ishiwata, Yukishige Ito, Xue-Wei Liu, Feiqing Ding

Summary: This study presents a glucosylation strategy using ZnI2 for stereoselective construction of 1,2-cis-O-glycosidic linkages. The versatility of this approach was demonstrated with various acceptors, including complex alcohols, indicating the potential for modular synthesis of various alpha-glucans.

ORGANIC LETTERS (2021)

Article Chemistry, Medicinal

Built-in adjuvants for use in vaccines

Qianqian Li, Zhimei Li, Nan Deng, Feiqing Ding, Yiliang Li, Hui Cai

Summary: This review primarily focuses on chemically synthesized compounds that can be used as built-in adjuvants, with a classification based on the induced immune activation mechanism and their application in various vaccine types.

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY (2022)

Article Chemistry, Organic

Zinc(II) Iodide-Directed β-Mannosylation: Reaction Selectivity, Mode, and Application

Xuemei Zhong, Siai Zhou, Jiaming Ao, Aoxin Guo, Qian Xiao, Yan Huang, Wanmeng Zhu, Hui Cai, Akihiro Ishiwata, Yukishige Ito, Xue-Wei Liu, Feiqing Ding

Summary: The study presents a strategy for direct mannosylation mediated by ZnI2, allowing for highly stereoselective construction of 1,2-cis-beta linkages, which can be applied to various alcohol acceptors for beta-mannosylation and modular synthesis of trisaccharides for N-glycan synthesis. Theoretical investigations using density functional theory calculations elucidated the mechanistic details of this beta-selective mannosylation.

JOURNAL OF ORGANIC CHEMISTRY (2021)

Review Chemistry, Multidisciplinary

Recent Chemical and Chemoenzymatic Strategies to Complex-Type N-Glycans

Xiaoya Zhao, Yan Huang, Siai Zhou, Jiaming Ao, Hui Cai, Katsunori Tanaka, Yukishige Ito, Akihiro Ishiwata, Feiqing Ding

Summary: Glycosylation is a major form of protein post-translational modification, and N-glycans play a crucial role in intercellular interaction and immune function. Efficient methods to provide homogeneous complex-type N-glycans have been urgently needed for analytical and medicinal purposes. Significant progress has been made in both chemical and chemoenzymatic strategies for the synthesis of N-glycans.

FRONTIERS IN CHEMISTRY (2022)

Article Chemistry, Organic

ZnI2-Mediated β-Galactosylation of C2-Ether-Type Donor

Siai Zhou, Jiaming Ao, Aoxin Guo, Xiaoya Zhao, Nan Deng, Guoqing Wang, Qixuan Yang, Akihiro Ishiwata, Xue-Wei Liu, Qianqian Li, Hui Cai, Feiqing Ding

Summary: A versatile ZnI2-directed fi-galactosylation approach using a 4,6-O-tethered and 2-O-Bn galactosyl donor is reported for the stereoselective and efficient synthesis of fi-O-galactosides. The reaction tolerates a wide range of functional groups and complex molecular architectures, providing stereocontrolled fi-galactosides in moderate to excellent yields. The practicality of this transformation is demonstrated through the synthesis of a tetrasaccharide arabinogalactan fragment with high stereoselectivity.

ORGANIC LETTERS (2022)

Review Chemistry, Multidisciplinary

Recent advances in stereoselective 1,2-cis-O-glycosylations

Akihiro Ishiwata, Katsunori Tanaka, Jiaming Ao, Feiqing Ding, Yukishige Ito

Summary: 1,2-cis-O-glycosylation is essential in the assembly of bioactive glycans with various functions. However, controlling the stereoselectivity of glycosylation and specifically forming 1,2-cis glycosides is challenging. Recent advances in glycosyl donor modification, reaction conditions, and activation methods have been made in the development of 1,2-cis selective glycosylations.

FRONTIERS IN CHEMISTRY (2022)

Review Chemistry, Multidisciplinary

Molecularly Stimuli-Responsive Self-Assembled Peptide Nanoparticles for Targeted Imaging and Therapy

Yang Zhou, Qianqian Li, Ye Wu, Xinyu Li, Ya Zhou, Zhu Wang, Hui Liang, Feiqing Ding, Sheng Hong, Nicole F. Steinmetz, Hui Cai

Summary: Self-assembly is a widely used method for constructing biomaterials, and peptides have been extensively investigated due to their desirable properties. Stimuli-responsive peptide nanoparticles, capable of conformational and chemical changes in response to stimuli, have emerged as a promising class of materials with diverse biomedical applications.

ACS NANO (2023)

Review Biochemistry & Molecular Biology

Strategies for Synthesizing and Enhancing the Immune Response of Cancer Vaccines Based on MUC1 Glycopeptide Antigens

Lixin Yin, Yang Zhou, Sheng Hong, Feiqing Ding, Hui Cai

Summary: Cancer vaccines harness the patient's immune system to induce a specific immune response to kill cancer cells. Glycoprotein mucin 1 (MUC1) is a promising candidate for cancer vaccines but faces challenges due to poor immunogenicity. Conjugation with immune activators is necessary. This review focuses on MUC1 glycopeptide synthesis, advanced vaccine designs, and a comparison of different strategies.

CHEMBIOCHEM (2023)

Article Chemistry, Multidisciplinary

Theoretical studies on substrate-controlled selectivity of nickel-catalyzed hydroalkylation of 1,3-dienes

Yuhua Liu, Difei Liu, Senyu He, Xiaofeng Huang, Feiqing Ding, Yang Zhang

Summary: The mechanism of nickel-catalyzed selective hydroalkylation of 2-aryl-1,3-dienes was investigated using DFT calculations. The rate-determining step was found to be the ligand-to-ligand hydrogen transfer (LLHT) process. The LLHT step exhibits the lowest activation barrier when hydrogen transfers to the least sterically hindered position of the diene, forming a stable allylic-Ni intermediate. The subsequent nucleophilic attack leads to regio-divergent products depending on the substrate type, with steric effects playing a role in product selectivity.

NEW JOURNAL OF CHEMISTRY (2023)

Article Chemistry, Organic

An experimental and theoretical study on stereocontrolled glycosylations by a one-pot procedure

Xuemei Zhong, Xiaoya Zhao, Jiaming Ao, Yan Huang, Yuhua Liu, Siai Zhou, Bizhi Li, Akihiro Ishiwata, Qianglin Fang, Chongguang Yang, Hui Cai, Feiqing Ding

Summary: This study presents a one-pot strategy for stereocontrolled glycosylation to generate both alpha- and beta-glycosides by altering reaction conditions. The selective formation of beta-glycosides was achieved by activating the perbenzylated trichloroacetimidate with a catalytic amount of SnCl4 at -40 degrees C. On the other hand, alpha-glycosides were obtained as the major products at room temperature by using 3.0 equivalents of SnCl4 and/or TiCl4. Control experiments and DFT calculations provided mechanistic insights into the glycosylation reaction, revealing a sequential occurrence of beta-glycosylation and anomerization.

ORGANIC CHEMISTRY FRONTIERS (2022)

Article Chemistry, Multidisciplinary

Mechanistic insights into the palladium-catalyzed hydroaminocarbonylation of alkenes

Yuhua Liu, Feiqing Ding, Yixing Chen, Wenji Wu, Yusen He

Summary: DFT calculations were conducted on the Pd-catalyzed regioselective hydroaminocarbonylation of alkenes, revealing the significant impact of ligand electronic and steric effects on selectivity.

NEW JOURNAL OF CHEMISTRY (2021)

Article Chemistry, Organic

Systematic synthesis of novel phosphoglycolipid analogues as potential agonists of GPR55

Junpei Abe, Adam T. Guy, Feiqing Ding, Peter Greimel, Yoshio Hirabayashi, Hiroyuki Kamiguchi, Yukishige Ito

ORGANIC & BIOMOLECULAR CHEMISTRY (2020)

Article Chemistry, Organic

Pyrrolidine-based C1-symmetric chiral transition metal complexes as catalysts in the asymmetric organic transformations

Geeta Devi Yadav, Pooja Chaudhary, Balaram Pani, Surendra Singh

Summary: Chiral transition metal complexes with privileged ligands are efficient catalysts for various asymmetric organic transformations. Transition metal complexes of C1-symmetric pyrrolidine-based ligands have been widely used in asymmetric organic reactions. However, a comprehensive review article on the transition metal complexes of chiral C1-symmetric pyrrolidine-based ligands derived from (L)-proline has not been published.

TETRAHEDRON LETTERS (2024)