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Glycosyl Bunte Salts: A Class of Intermediates for Sugar Chemistry
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    Glycosyl Bunte Salts: A Class of Intermediates for Sugar Chemistry
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    Department of Biomolecular Engineering, Graduate School of Engineering, Tohoku University, Sendai 980-8579, Japan
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    Organic Letters

    Cite this: Org. Lett. 2018, 20, 1, 76–79
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    https://doi.org/10.1021/acs.orglett.7b03400
    Published December 15, 2017
    Copyright © 2017 American Chemical Society

    Abstract

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    S-Glycosyl thiosulfates have been discovered as a new class of synthetic intermediates in sugar chemistry, named “glycosyl Bunte salts” after 19th-century German chemist, Hans Bunte. The synthesis was achieved by direct condensation of unprotected sugars and sodium thiosulfate using a formamidine-type dehydrating agent in water–acetonitrile mixed solvent. The application of glycosyl Bunte salts is demonstrated with transformation reactions into other glycosyl compounds such as a 1-thio sugar, a glycosyl disulfide, a 1,6-anhydro sugar, and an O-glycoside.

    Copyright © 2017 American Chemical Society

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    This article is cited by 26 publications.

    1. Neha Sharma Prabhakar, Kaushal Kishor, Krishna Nand Singh. Easy Access to α-Ketothioamides via Oxidative Amidation of Bunte Salts Using Electrolysis or Hypervalent Iodine. The Journal of Organic Chemistry 2024, 89 (18) , 13329-13337. https://doi.org/10.1021/acs.joc.4c01450
    2. Jie Huang, Jin-Quan Li, Xin-Yue Cui, Yi-Han Qin, Shi-Jie Ma, Zi-An An, Wen-Wu Sun, Bin Wu. A Method for the Synthesis of Thioindoles through Copper-Catalyzed C–S Bond Coupling Reaction. The Journal of Organic Chemistry 2024, 89 (1) , 245-256. https://doi.org/10.1021/acs.joc.3c02008
    3. Xin Qiu, Daniel Chong, Antony J. Fairbanks. Selective Anomeric Acetylation of Unprotected Sugars with Acetic Anhydride in Water. Organic Letters 2023, 25 (11) , 1989-1993. https://doi.org/10.1021/acs.orglett.3c00584
    4. Jie Huang, Wen-Wu Sun, Jin-Quan Li, Ao-Di Ma, Ji-Kai Liu, Bin Wu. Copper-Catalyzed C2- or C3-Thioglycosylation of Indoles with N-(Thioglycosides)succinimides: An Effective Strategy for the Total Synthesis of Isatindigotindolosides. Organic Letters 2023, 25 (3) , 528-532. https://doi.org/10.1021/acs.orglett.2c04270
    5. Xin Qiu, Antony J. Fairbanks. Direct Synthesis of para-Nitrophenyl Glycosides from Reducing Sugars in Water. Organic Letters 2020, 22 (6) , 2490-2493. https://doi.org/10.1021/acs.orglett.0c00728
    6. Xiantao Ma, Jing Yu, Ran Yan, Mengli Yan, Qing Xu. Promoting Effect of Crystal Water Leading to Catalyst-Free Synthesis of Heteroaryl Thioether from Heteroaryl Chloride, Sodium Thiosulfate Pentahydrate, and Alcohol. The Journal of Organic Chemistry 2019, 84 (17) , 11294-11300. https://doi.org/10.1021/acs.joc.9b01670
    7. Govind P. Singh, Flinta E.D. Wilson, Nathan H. Reid, Antony J. Fairbanks. One step aqueous synthesis of unprotected glycosyl C-sulfonates. Carbohydrate Research 2025, 551 , 109411. https://doi.org/10.1016/j.carres.2025.109411
    8. Weizhun Yang, Sherif Ramadan, Yan Zu, Mengxia Sun, Xuefei Huang, Biao Yu. Chemical synthesis and functional evaluation of glycopeptides and glycoproteins containing rare glycosyl amino acid linkages. Natural Product Reports 2024, 41 (9) , 1403-1440. https://doi.org/10.1039/D4NP00017J
    9. Monalisa Kundu, Anup Kumar Misra. Preparation of glycosyl disulfides and sulfides via the formation of glycosyl Bunte salts as thiol surrogates. Tetrahedron 2024, 158 , 132242. https://doi.org/10.1016/j.tet.2021.132242
    10. Smritilekha Bera, Dhananjoy Mondal, Bhaskar Chatterjee. Application of N-Bromosuccinimide in Carbohydrate Chemistry. SynOpen 2023, 07 (04) , 501-510. https://doi.org/10.1055/s-0042-1751501
    11. Yasuhiro Meguro, Masaru Enomoto, Shigefumi Kuwahara. Synthesis of the N ‐Amykitanosyl Tetramic Acid Moiety of Amycolamicin. European Journal of Organic Chemistry 2023, 26 (13) https://doi.org/10.1002/ejoc.202300075
    12. Gefei Li, Jie Jing, Zhenyang Luo, Juan Mo, Decai Xiong, Xinshan Ye. Recent Advances in Protection-Free Glycosylations. Chinese Journal of Organic Chemistry 2023, 43 (6) , 1991. https://doi.org/10.6023/cjoc202211024
    13. Yu Hamaya, Naoko Komura, Akihiro Imamura, Hideharu Ishida, Hiromune Ando, Hide-Nori Tanaka. Protecting-group- and microwave-free synthesis of β-glycosyl esters and aryl β-glycosides of N-acetyl-d-glucosamine. Bioorganic & Medicinal Chemistry 2022, 67 , 116852. https://doi.org/10.1016/j.bmc.2022.116852
    14. Xin Qiu, Anna L. Garden, Antony J. Fairbanks. Protecting group free glycosylation: one-pot stereocontrolled access to 1,2- trans glycosides and (1→6)-linked disaccharides of 2-acetamido sugars. Chemical Science 2022, 13 (14) , 4122-4130. https://doi.org/10.1039/D2SC00222A
    15. Kalyan Dey, Narayanaswamy Jayaraman. Anomeric alkylations and acylations of unprotected mono- and disaccharides mediated by pyridoneimine in aqueous solutions. Chemical Communications 2022, 58 (13) , 2224-2227. https://doi.org/10.1039/D1CC07056H
    16. Marco Brito-Arias. Glycosides, Synthesis and Characterization. 2022, 1-100. https://doi.org/10.1007/978-3-030-97854-9_1
    17. Raoul Walther, Alexander N. Zelikin. Chemical (neo)glycosylation of biological drugs. Advanced Drug Delivery Reviews 2021, 171 , 62-76. https://doi.org/10.1016/j.addr.2021.01.021
    18. Károly Ágoston, Gregory M. Watt. Methods for O-Glycoside Synthesis. 2021, 103-159. https://doi.org/10.1016/B978-0-12-819475-1.00017-1
    19. Antony J. Fairbanks. Applications of Shoda's reagent (DMC) and analogues for activation of the anomeric centre of unprotected carbohydrates. Carbohydrate Research 2021, 499 , 108197. https://doi.org/10.1016/j.carres.2020.108197
    20. Xin Qiu, Antony J. Fairbanks. Scope of the DMC mediated glycosylation of unprotected sugars with phenols in aqueous solution. Organic & Biomolecular Chemistry 2020, 18 (37) , 7355-7365. https://doi.org/10.1039/D0OB01727B
    21. Yasuhiro Meguro, Masato Noguchi, Gefei Li, Shin-ichiro Shoda. Efficient generation of thiolate sugars from glycosyl Bunte salts and its application to S-glycoside synthesis. Tetrahedron Letters 2020, 61 (32) , 152198. https://doi.org/10.1016/j.tetlet.2020.152198
    22. Tomonari Tanaka. [Review] Synthesis of Glycosyl Derivatives and Glycomaterials Based on Direct Activation of Unprotected Sugars. Bulletin of Applied Glycoscience 2019, 9 (1) , 17-27. https://doi.org/10.5458/bag.9.1_17
    23. Antony J. Fairbanks. Meet the Board of ChemistryOpen : Antony J. Fairbanks. ChemistryOpen 2019, 8 (2) , 188-189. https://doi.org/10.1002/open.201900020
    24. Chunlai Feng, Jin Wang, Qiujie Tang, Zijian Zhong, Shusen Qiao, Xingyu Liu, Can Chen, Aihua Zhou. One-pot synthesis of glycosyl phenylthiosulfonates from sulfinate, S and glycosyl bromides. Carbohydrate Research 2019, 471 , 1-5. https://doi.org/10.1016/j.carres.2018.10.005
    25. Guoqing Li, Guomeng Zhang, Xuewu Deng, Kunyu Qu, Hua Wang, Wei Wei, Daoshan Yang. Transition-metal-free KI-catalyzed regioselective sulfenylation of 4-anilinocoumarins using Bunte salts. Organic & Biomolecular Chemistry 2018, 16 (43) , 8015-8019. https://doi.org/10.1039/C8OB02268B
    26. Madhu Babu Tatina, Duc Thinh Khong, Zaher M. A. Judeh. Efficient Synthesis of α‐Glycosyl Chlorides Using 2‐Chloro‐1,3‐dimethylimidazolinium Chloride: A Convenient Protocol for Quick One‐Pot Glycosylation. European Journal of Organic Chemistry 2018, 2018 (19) , 2208-2213. https://doi.org/10.1002/ejoc.201800360

    Organic Letters

    Cite this: Org. Lett. 2018, 20, 1, 76–79
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.orglett.7b03400
    Published December 15, 2017
    Copyright © 2017 American Chemical Society

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