Article
Chemistry, Organic
Rui Yang, Haiqing He, Zixi Chen, Yingying Huang, Guozhi Xiao
Summary: The study presents a one-pot glycosylation strategy for synthesizing both glycans and nucleosides based on ortho-(1-phenylvinyl)benzyl glycosides. It offers several advantages such as no aglycon transfers, no interference of departing species, and no unpleasant odor, and allows for the construction of up to four different glycosidic linkages.
Article
Chemistry, Organic
Zhiyuan Chen, Guozhi Xiao
Summary: The highly branched tetradecasaccharide repeating unit and shorter sequences of GLSWA-1 from Ganoderma lucidum, which possess immune-enhancing activities, were prepared using a one-pot glycan assembly strategy that features orthogonal one-pot glycosylation, one-pot assembly of oligosaccharides, and modular and convergent [4+5+5] assembly of the highly branched tetradecasaccharide.
Article
Chemistry, Multidisciplinary
Hui Liu, Zhi-Fen Liang, Han-Jian Liu, Jin-Xi Liao, Li-Jun Zhong, Yuan-Hong Tu, Qing-Ju Zhang, Bin Xiong, Jian-Song Sun
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)
Article
Chemistry, Multidisciplinary
Yunqin Zhang, Yanlei Hu, Shanshan Liu, Haiqing He, Roujing Sun, Gang Lu, Guozhi Xiao
Summary: This paper reports an efficient, stereoselective and orthogonal one-pot synthesis of a tetradecasaccharide and shorter sequences from Lentinus giganteus polysaccharides. The method utilizes newly developed merging reagent modulation and remote anchimeric assistance for highly stereoselective glycosylation reactions. This method has mild reaction conditions, broad substrate scopes and significantly shortened step counts.
Article
Chemistry, Organic
Yuxin Ma, Qiong Jiang, Xiufang Wang, Guozhi Xiao
Summary: In this study, Cordyceps militaris glycans with potent antioxidant activities were efficiently synthesized using innovative approaches.
Article
Chemistry, Organic
Si-Yu Zhou, Xin-Ping Hu, Hui-Juan Liu, Qing-Ju Zhang, Jin-Xi Liao, Yuan-Hong Tu, Jian-Song Sun
Summary: A novel and efficient glycosylation protocol has been established using MTAEN glycoside as donors, featuring stable donors, mild catalytic conditions, broad substrate scope, and versatility in various one-pot strategies for efficient synthesis of oligosaccharides.
Article
Chemistry, Organic
Rui Yang, Xingchun Sun, Yunqin Zhang, Guozhi Xiao
Summary: Efficient and collective synthesis of rhynchosporosides, which cause scald diseases, has been achieved through an orthogonal one-pot glycosylation strategy based on PTFAI glycosylation, Yu glycosylation, and PVB glycosylation. This strategy incorporates reagent modulation and remote anchimeric assistance (RMRAA) alpha-glucosylation strategies, overcoming issues encountered in thioglycoside-based orthogonal one-pot glycosylation and streamlining glycan chemical synthesis.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Review
Chemistry, Organic
Kotaro Kikushima, Elghareeb E. Elboray, J. Oscar C. Jimenez-Halla, Cesar R. Solorio-Alvarado, Toshifumi Dohi
Summary: This review summarizes the double functionalization of carbon-iodine(iii) and ortho carbon-hydrogen bonds using diaryliodonium(iii) salts, which has significant application value in molecular synthesis.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Organic
Mattis Damrath, Lucien D. Caspers, Daniel Duvinage, Boris J. Nachtsheim
Summary: Two simple methods for synthesizing O- and N-bridged diaryliodonium triflates are described. Different derivatizations were applied to demonstrate their usefulness as building blocks and to gain a deeper understanding of their general reactivity.
Article
Chemistry, Organic
Penghua Li, Hanyingzi Fan, Qiang Tan, Guozhi Xiao
Summary: Highly stereoselective construction of 1,2-cis-Arap linkages has been achieved with a broad range of alcoholic acceptors, including strong nucleophiles and complex bioactive molecules. This method was applied to a regioselective and orthogonal one-pot synthesis of a pentasaccharide, which serves as the structural motif of a side chain in type II arabinogalactan.
Article
Chemistry, Organic
Bei-Bei Zhan, Kai-Sheng Xie, Qian Zhu, Weiping Zhou, Dapeng Zhu, Biao Yu
Summary: A Cu-(OTf)(2)-catalyzed glycosylation protocol using glycosyl ortho-N-phthalimidoylpropynyl benzoates(NPPBs) as donors was developed, which exhibits an inexpensive catalyst, convenient conditions, high to excellent yields, and a broad substrate scope. Mechanistic studies showed the formation of an isochromen-4-ylcopper-(II) intermediate upon leaving group departure.
Article
Chemistry, Multidisciplinary
Hirofumi Endo, Masaharu Ochi, Md Azadur Rahman, Tomoaki Hamada, Takahiro Kawano, Toshiki Nokami
Summary: Unnatural cyclic oligosaccharides composed of N-acetylglucosamine with alpha-1,4-glycosidic linkages have been successfully synthesized using electrochemical synthesis. The study also demonstrated that this method can be utilized for the isomerization of linear oligosaccharides and intramolecular glycosylation for cyclization.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Anze Zupanc, Marjan Jereb
Summary: This study presents the synthesis and characterization of N-iodo sulfoximines, with a one-pot cascade reaction yielding high isolated yields and demonstrating the iodination of aryls, oxidation, and conversion to N-SCF3 congeners.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Monika Bhardwaj, Debaraj Mukherjee
Summary: This study reports a new method for the rapid synthesis of 2-deoxy-3-thio pyranoses and their O-glycosides through the reaction of glycals with two different types of nucleophiles in the presence of SnCl4. The reaction involves thioaryl substitution at C-3 and alpha-selective O-glycosylation at C-1, combining two reactions with three interventions. The method offers operational simplicity at 0 degrees C in 10-20 minutes and is compatible with a wide range of primary and secondary alcohols, yielding products in good to excellent yields. Moreover, the strategy has the potential for the synthesis of various natural products and drug molecules, as supported by control experiments.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Manuel G. Schriefer, Laura Treiber, Rainer Schobert
Summary: A convergent total synthesis of bacterial gyrase B/topoisomerase IV inhibitor kibdelomycin was successfully accomplished. The synthesis started from inexpensive d-mannose and l-rhamnose, which were converted into N-acylated amycolose and amykitanose derivatives. The decalin core was constructed via an intramolecular Diels-Alder reaction. The total synthesis was achieved in 2.8% overall yield using previously published methods, and an alternative order of connecting the essential fragments was also made possible.
Article
Chemistry, Organic
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)
