Article
Chemistry, Organic
Jianhong Zhang, Tetsuo Koyama, Takahiko Matsushita, Ken Hatano, Koji Matsuoka
Summary: Efficient synthesis of lauryl thioglycoside of Neu5Gc was achieved from a known thioglycoside of Neu5Ac. The reactivity of Neu5Gc thioglycoside in O-glycosidation was investigated, showing good activities with simple alcohols. The thioglycoside also demonstrated potential as a glycosyl donor in reactions with glucose and lactose derivatives.
TETRAHEDRON LETTERS
(2021)
Article
Chemistry, Organic
Tiffany Duong, Erik Alvarez Valenzuela, Justin R. Ragains
Summary: In this study, we demonstrate that the reaction between benzylchalcogenoglycosides and benzyne in the presence of alcohols can proceed highly 1,2-cis-selective O-glycosylation in a solvent-dependent manner. Thioglycosides, selenoglycosides, and alcohols with different nucleophilicities can participate in the reaction, and the need for unusual protecting groups, auxiliary groups, and additives is eliminated.
Article
Chemistry, Organic
Maria A. Boulogeorgou, Alexandros Toskas, John K. Gallos, Christos I. Stathakis
Summary: A direct and practical method for oxidative anomeric O-glycosylation of glycosyl iodides with various alcohols as glycosyl acceptors is presented. By using phenyliodine(iii) diacetate (PIDA) as the promoter, the reaction can be carried out at ambient temperature, providing environmentally friendly and operationally simple access to 1,2-trans-O-glycosides.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Organic
Rongkun Liu, Qingting Hua, Qixin Lou, Jiazhe Wang, Xiaona Li, Zhi Ma, You Yang
Summary: The study presents an efficient glycosidation method using NIS/TMSOTf as promoters and glycosyl ortho-hexynylbenzoates as donors for the synthesis of O-glycosides and nucleosides. This approach offers mild reaction conditions, cheap promoters, wide substrate scope, and good to excellent yields. Additionally, the method shows promise in constructing challenging O- and N-glycosidic linkages and synthesizing oligosaccharides efficiently.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Jincai Wang, Xinguang Lan, Shuangshuang Zhang, Chenglin Cai, Qi Zhang, Yingle Feng, Yonghai Chai
Summary: We have developed a new type of donor, S-o-(p-methoxyphenylethynyl)benzyl, for highly efficient glycosylation. This donor, activated by 10% Tf2O, successfully underwent glycosylation with various acceptors, resulting in excellent yield of corresponding glycosides. In addition, we combined the single-catalyst one-pot and latent-activestrategies for the first time to prepare two repetitive fragments of Polyporus umbellatus polysaccharides (PUPs) for future studies on the structure-activity relationship of PUPs.
Article
Chemistry, Organic
Jordi Mestre, Isabel Bascuas, Miguel Bernus, Sergio Castillon, Omar Boutureira
Summary: Fluorinated carbohydrate mimetics are important in Glycoscience, but the synthesis of complex C(sp(3))-CF3 congeners is underdeveloped. A new protocol for preparing 2-deoxy-2-trifluoromethyl-d-hexopyranosides from d-glycals is presented. The stereoselectivity of glycosylation is mainly controlled by electronic and steric factors, resulting in the formation of 1,2-trans glycosides due to the configuration of the CF3 moiety at C-2. This approach was successfully applied in the synthesis of 2-CF3-glycoconjugates of natural origin.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Multidisciplinary
Samira Escopy, Yashapal Singh, Keith J. Stine, Alexei V. Demchenko
Summary: This research describes a direct conversion of thioglycosides using a regenerative approach, bypassing the need for bromide intermediates and heavy-metal-based promoters. The reaction conditions are mild, with only 1 equiv. NIS and catalytic HOFox needed under neutral conditions.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Organic
Nicholas W. See, Xiaowen Xu, Vito Ferro
Summary: A safe and operationally simple method for the preparation of fi-D-glycosyl fluorides has been presented, demonstrating the facile, high-yielding, and diastereoselective conversions of 2-O-acyl thioglycosides to fi-D- and other 1,2-trans glycosyl fluorides through a precise combination of XtalFluor-M, N-bromosuccinimide, and Et3N·3HF. The roles of these reagents and their interplay on fluorination stereoselectivity are dissected in this study.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Jinsheng Lai, Shuqin Wu, Zhuoyi Zhou, Hui Liu, Yuanhong Tu, Qingju Zhang, Liming Wang
Summary: A novel exclusive β-selective O-aryl glycosylation method was developed using glycosyl chloride and arylboronic acid with a palladium catalyst under an air atmosphere. The reaction was insensitive to moisture and utilized readily available and bench-stable substrates. It exhibited good tolerance towards various arylboronic acids and glycosyl chloride donors. The oxidation of arylboronic acid by O-2 in air produced phenol as the aromatic source. This new strategy offers an alternative route for the efficient synthesis of bioactive O-aryl glycosides and may have broad applications in the future.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Yingying Liu, Xiaojin Tu, Xiaoxiao Wei, Dongdong Wang, Xiaoran Zhang, Wei Chen, Chen Chen, Shuangyin Wang
Summary: This study investigates the influence of catalyst surface properties on molecular adsorption configuration and electrocatalytic urea synthesis activity, and finds that a negatively charged surface can induce a C-bound path and enhance urea synthesis.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Qiuyu Zhu, Yu Tang, Biao Yu
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.
Article
Chemistry, Multidisciplinary
Shiyun He, Jinyu Hou, Meiling Ye, Jian Chen, Guanghui Lv, Tianle Huang, Zhongzhen Yang, Yong Wu
Summary: A visible-light-mediated glycosylation reaction has been reported, which efficiently produces S-aryl glycosides. The reaction proceeds through an EDA complex. This method shows potential applications in late-stage functionalisation of drug molecules and large-scale experiments.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Physical
Tong Li, Tianlu Li, Haoru Zhuang, Fengshan Wang, Richard R. Schmidt, Peng Peng
Summary: Stereo- and regioselective glycosidation remains a significant challenge in carbohydrate chemistry. Acid-base catalysis, particularly in O-glycosyl trichloroacetimidate activation, offers an alternative pathway with increased proton acidity and oxygen nucleophilicity for selective glycosidation. Platinum(IV) chloride serves as an ideal catalyst due to its weak Lewis acid properties and bidentate ligation capacity, enabling predominantly beta-configuration glycosidation products and regioselectivity in various carbohydrate acceptor moieties.
Article
Chemistry, Multidisciplinary
Guiying He, Kaia R. Parenti, Luis M. Campos, Matthew Y. Sfeir
Summary: Singlet fission refers to the process of generating two triplet excitons from a single absorbed photon. However, there are ambiguities in this definition due to the complexity of double triplet states and their interconversion processes. Traditional models depict singlet fission as a sequential two-step conversion, but they overlook the possibility of directly harvesting energy from coupled triplet pairs. This study demonstrates the direct extraction of individual triplet excitons from bound triplet pairs and quantifies the energy harvesting efficiency using unique spectral and kinetic features.
ADVANCED MATERIALS
(2022)
Review
Chemistry, Organic
Shuai Meng, Xiaohua Li, Jianglong Zhu
Summary: The article summarizes the research advances in the direct synthesis of 2-deoxy glycosides, with a particular emphasis on studies published in the last five years. It also discusses some recent reports on the stereoselective synthesis of 2-deoxy thioglycosides.
Article
Chemistry, Organic
Adam H. Trotta
Article
Chemistry, Organic
Adam H. Trotta
JOURNAL OF ORGANIC CHEMISTRY
(2017)
Article
Polymer Science
Ferdinando F. Bruno, Adam Trotta, Stephen Fossey, Subhalakshmi Nagarajan, Ramaswamy Nagarajan, Lynne A. Samuelson, Jayant Kumar
JOURNAL OF MACROMOLECULAR SCIENCE PART A-PURE AND APPLIED CHEMISTRY
(2010)
Article
Chemistry, Multidisciplinary
Trevor C. Sherwood, Adam H. Trotta, Scott A. Snyder
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2014)
Article
Chemistry, Organic
Faiza Diaba, Gisela Trenchs
Summary: The first violet light-mediated synthesis of gamma- and delta-lactams from N-alkenyl trichloroacetamides is reported in this paper. The reactions are conducted in tetrahydrofuran or 2-methyltetrahydrofuran as the sole solvent without catalysts or additives, under non-anhydrous conditions in an air atmosphere where the solvent serves as the radical initiator.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Feroze Hussain, Sajjad Ahmed, Ashiq Hussain Padder, Qazi Naveed Ahmed
Summary: This study reports a novel and efficient one-pot synthesis method for mixed phosphorotrithioates, which does not require supplementary additives and shows broad applicability.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Hyunjin Oh, Ikyon Kim
Summary: A new 1,2,4-triazole-pyrrolo[1,2-a]pyrazine hybrid system, 6-acylpyrrolo[1,2-a][1,2,4]triazolo[5,1-c]pyrazine, was synthesized using a catalyst-free method. This method involved sequential exposure of pyrrole-2-carbonitrile-derived substrates to DMF-DMA and acyl hydrazide, resulting in the formation of acylated pyrazine and 1,2,4-triazole rings, enabling the installation of various substituents at specific positions on the core skeleton.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Ming Yan, Si-fan Wang, Yong-po Zhang, Jin-zhong Zhao, Zhuo Tang, Guang-xun Li
Summary: Here we developed an efficient photocatalytic approach for the convenient preparation of sulfinamides. The reaction allows for the gram-scale preparation of sulfinamides and the one-pot synthesis of various sulfonyl amides.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Farzaneh Bandehali-Naeini, Zahra Tanbakouchian, Noushin Farajinia-Lehi, Nicolas Mayer, Morteza Shiri, Martin Breugst
Summary: Two tandem catalytic systems were developed for the synthesis of novel 3,4-disubstituted maleimides using the same Ugi adducts. Different maleimide structures can be synthesized using either Pd or Cu catalysis.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Tanya Raghava, Anjan Chattopadhyay, Subhadeep Banerjee, Nivedita Sarkar
Summary: Amine substitution of two ortho fluorine atoms of tetrafluoroterephthalonitrile through SNAr chemistry is easily achievable. But further fluorine substitution is only possible under forcing conditions, yielding valuable fluorophores for bioimaging.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Review
Chemistry, Organic
Anju Chadha, Santosh Kumar Padhi, Selvaraj Stella, Sowmyalakshmi Venkataraman, Thangavelu Saravanan
Summary: Alcohol dehydrogenases are enzymes that use cofactors for oxidation or reduction reactions of alcohols or carbonyl compounds. They are utilized in green chemistry and have applications in the production of pharmaceuticals. Recombinant enzymes have solved the challenge of producing purified enzymes in large quantities. Engineered alcohol dehydrogenases have been used in asymmetric synthesis in industry. Various methods have been established for regenerating expensive cofactors to make the enzymatic process more efficient and economically viable.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)