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DOI: 10.1055/a-2348-2803
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Carbohydrate Chemistry in China

Highly Regio-/Stereoselective Synthesis of Carbohydrates with Unsaturated Glycosyl Donors under Mild Conditions

Xinyu Gao
a   Hubei Key Laboratory of Natural Products Research and Development, College of Biological and Pharmaceutical Sciences, China Three Gorges University, Yichang 443002, P. R. of China
,
Keke Ren
a   Hubei Key Laboratory of Natural Products Research and Development, College of Biological and Pharmaceutical Sciences, China Three Gorges University, Yichang 443002, P. R. of China
,
Lijuan Ma
a   Hubei Key Laboratory of Natural Products Research and Development, College of Biological and Pharmaceutical Sciences, China Three Gorges University, Yichang 443002, P. R. of China
,
Nengzhong Wang∗
a   Hubei Key Laboratory of Natural Products Research and Development, College of Biological and Pharmaceutical Sciences, China Three Gorges University, Yichang 443002, P. R. of China
b   Hubei Three Gorges Laboratory, Yichang 443007, P. R. of China
,
Nianyu Huang  ∗
a   Hubei Key Laboratory of Natural Products Research and Development, College of Biological and Pharmaceutical Sciences, China Three Gorges University, Yichang 443002, P. R. of China
b   Hubei Three Gorges Laboratory, Yichang 443007, P. R. of China
,
Hui Yao  ∗
a   Hubei Key Laboratory of Natural Products Research and Development, College of Biological and Pharmaceutical Sciences, China Three Gorges University, Yichang 443002, P. R. of China
b   Hubei Three Gorges Laboratory, Yichang 443007, P. R. of China
› Author AffiliationsThis work was partially supported by the National Natural Science Foundation of China (22207063), Higher Education Discipline Innovation Project (111 Project, D20015), the Natural Science Foundation of Hubei Province (2022CFB838), the Hubei Provincial Department of Education (D20221204, Q20221212), and the Natural Science Foundation of Yichang Municipality (A23-2-002).
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Abstract

Carbohydrates and their conjugates play important roles in life activities and drug development. Our group was committed to the general and effective glycosylation methods and their application in chemical biology using unsaturated glycosyl donors. In the past five years, we have reported several synthetic strategies with high stereoselectivity and milder conditions compared with previous works. In particular, high chemo-/regio- and stereoselective O-glycosylation, C-glycosylation and S-glycosylation could be achieved via palladium catalysis under open-air conditions at room temperature. In this Account, we will introduce our research progress in constructing four types of glycosides.

1 Introduction

2 Stereoselective Synthesis of O-Glycosides

3 Stereoselective Synthesis of C-Glycosides

4 Stereoselective Synthesis of N-Glycosides

5 Stereoselective Synthesis of S-Glycosides

6 Conclusion

Key words

glycosylation - transition metal catalysis - unsaturated glycosyl donors - stereoselectivity - carbohydrates


Publication History

Received: 30 April 2024

Accepted after revision: 18 June 2024

Accepted Manuscript online:
19 June 2024

Article published online:
10 July 2024

© 2024. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 

  • References

    • 2a Huang W, Fan S, Gao J, Luo S, Tang S, Liu J, Wang X. Angew. Chem. Int. Ed. 2022; 61: e202204907
      CrossrefPubMed
    • 2b Qin C, Li L, Tian G, Ding M, Zhu S, Song W, Hu J, Seeberger PH, Yin J. J. Am. Chem. Soc. 2022; 144: 21068
      CrossrefPubMed
    • 2c Unione L, Ammerlaan AN. A, Bosman GP, Uslu E, Liang R, Broszeit F, van der WoudeR, Liu Y, Ma S, Liu L, Gómez-Redondo M, Bermejo IA, Valverde P, Diercks T, Ardá A, de Vries RP, Boons G.-J. Nat. Commun. 2024; 15: 2979
      CrossrefPubMed
    • 2d Yao W, Xiong D.-C, Yang Y, Geng C, Cong Z, Li F, Li B.-H, Qin X, Wang L.-N, Xue W.-Y, Yu N, Zhang H, Wu X, Liu M, Ye X.-S. Nat. Synth. 2022; 1: 854
      Crossref
    • 2e Ye F, Zhao J, Xu P, Liu X, Yu J, Shangguan W, Liu J, Luo X, Li C, Ying T, Wang J, Yu B, Wang P. Angew. Chem. Int. Ed. 2021; 60: 12904
      CrossrefPubMed
    • 3a Löwenberg B, Ossenkoppele GJ, van Putten W, Schouten HC, Graux C, Ferrant A, Sonneveld P, Maertens J, Jongen-Lavrencic M, von Lilienfeld-Toal M, Biemond BJ, Vellenga E, van Marwijk Kooy, Verdonck LF, Beck J, Döhner H, Gratwohl A, Pabst T, Verhoef G. N. Engl. J. Med. 2009; 361: 1235
      CrossrefPubMed
    • 3b Mannem RR, Thoti N, Aidhen IS. In Carbohydrates in Drug Discovery and Development 2020; 97
  • 4 Hiraizumi M, Akashi T, Murasaki K, Kishida H, Kumanomidou T, Torimoto N, Nureki O, Miyaguchi I. Nat. Struct. Mol. Biol. 2023; 31: 159
    CrossrefPubMed
    • 5a Kumavath R, Paul S, Pavithran H, Paul MK, Ghosh P, Barh D, Azevedo V. Biomolecules 2021; 11: 1275
      CrossrefPubMed
    • 5b Prassas I, Diamandis EP. Nat. Rev. Drug Discov. 2008; 7: 926
      CrossrefPubMed
    • 5c Wang JK. T, Portbury S, Thomas MB, Barney S, Ricca DJ, Morris DL, Warner DS, Lo DC. Proc. Natl. Acad. Sci. U.S.A. 2006; 103: 10461
      CrossrefPubMed
    • 5d Grynkiewicz G, Szeja W. J. Mol. Biomark. Diagn. 2015; 6: 100259
      Crossref
    • 5e Škubník J, Bejček J, Pavlíčková VS, Rimpelová S. Molecules 2021; 26: 5627
      CrossrefPubMed
    • 5f Maury Y, Poydenot P, Brinon B, Lesueur L, Gide J, Roquevière S, Côme J, Polvèche H, Auboeuf D, Denis JA, Pietu G, Furling D, Lechuga M, Baghdoyan S, Peschanski M, Martinat C. iScience 2019; 11: 258
      CrossrefPubMed
  • 6 Li L, Li Q, Gui L, Deng Y, Wang L, Jiao J, Hu Y, Lan X, Hou J, Li Y, Lu D. Bioact. Mater. 2023; 19: 24
    PubMed
  • 7 Abdel-Sattar E, Ali DE. Rev. Bras. Farmacogn. 2022; 32: 188
    CrossrefPubMed
    • 8a Allard B, Allard D, Buisseret L, Stagg J. Nat. Rev. Clin. Oncol. 2020; 17: 611
      CrossrefPubMed
    • 8b Stirrups R. Lancet Oncol. 2019; 20: e402
      CrossrefPubMed
  • 9 Yu C, Xu Y, Zeng M, Wang J, Dai W, Wang J, Liu H. Adv. Sci. 2024; 11: 230776
    • 10a Wiviott SD, Raz I, Bonaca MP, Mosenzon O, Kato ET, Cahn A, Silverman MG, Zelniker TA, Kuder JF, Murphy SA, Bhatt DL, Leiter LA, McGuire DK, Wilding JP. H, Ruff CT, Gause-Nilsson IA. M, Fredriksson M, Johansson PA, Langkilde A.-M, Sabatine MS. N. Engl. J. Med. 2019; 380: 347
      CrossrefPubMed
    • 10b Chang C, Ho Y, Lin S, Liu H. J. Diabetes Mellitus 2019; 9: 77
      Crossref
    • 10c Shao S, Zhang N, Specht GP, You S, Song L, Fu Q, Huang D, You H, Shu J, Domissy A, Li S, Nguyen-Tran V, Joseph SB, Chatterjee AK, Chen JJ, Schultz PG, Bollong MJ. Proc. Natl. Acad. Sci. U.S.A. 2024; 121: e2400077121
      CrossrefPubMed
  • 11 Roy R, Banerjee K, Bhattacharya R, Mukhopadhyay A. Ann. Oncol. 2016; 27: ix49
    Crossref
  • 12 Raninga P, Lee A, Sinha D, Shin Y.-Y, Mittal D, Kalimutho M, Khanna KK. Ann. Oncol. 2019; 30: v3
    Crossref
  • 13 Zhao Q, Wang M, Xu D, Zhang Q, Liu W. Nature 2015; 518: 115
    CrossrefPubMed
    • 14a David RFriend, Chang GW. J. Med. Chem. 1985; 28: 51
      CrossrefPubMed
    • 14b Louveau T, Osbourn A. Cold Spring Harbor Perspect. Biol. 2019; 11: a034744
      CrossrefPubMed
    • 14c Chen F, Huang G. Eur. J. Med. Chem. 2019; 182: 111612
      CrossrefPubMed
    • 15a Shi W, Zhang J, Liu L, Li W, Liu Z, Ren A, Wang J, Tang C, Yang Y, Xu D, Huang Q, Wang Y, Luo C, Huang W, Tang F. J. Med. Chem. 2022; 66: 1011
      CrossrefPubMed
    • 15b Wang J, Zhang Y, Zhu Y, Liu J, Chen Y, Cao X, Yang Y. Org. Lett. 2020; 22: 8780
      CrossrefPubMed
  • 16 Bennett CS, Galan MC. Chem. Rev. 2018; 118: 7931
    CrossrefPubMed
    • 17a Babu RS, Chen Q, Kang S.-W, Zhou M, O’Doherty GA. J. Am. Chem. Soc. 2012; 134: 11952
      CrossrefPubMed
    • 17b Zhang Y, Wang L, Zhou Q, Li Z, Li D, Yin C, Wang X, Xiao G. Angew. Chem. Int. Ed. 2023; 62: e202301351
      CrossrefPubMed
    • 18a Desai SP, Yatzoglou G, Turner JA, Taylor MS. J. Am. Chem. Soc. 2024; 146: 4973
      CrossrefPubMed
    • 18b Zeng J, Wang R, Zhang S, Fang J, Liu S, Sun G, Xu B, Xiao Y, Fu D, Zhang W, Hu Y, Wan Q. J. Am. Chem. Soc. 2019; 141: 8509
      CrossrefPubMed
  • 19 Tang X, Zhou Y, Wang Y, Lin Y, Pan S, Che Q, Sang J, Gao Z, Zhang W, Wang Y, Li G, Gao L, Wang Z, Yang X, Liu A, Wang S, Yu B, Xu P, Wang Z, Zhang Z, Yang P, Xie W, Sun H, Li W. J. Am. Chem. Soc. 2024; 146: 8768
    CrossrefPubMed
    • 20a Demkiw KM, Remmerswaal WA, Hansen T, van der Marel GA, Codée JD. C, Woerpel KA. Angew. Chem. Int. Ed. 2022; 61: e202209401
      CrossrefPubMed
    • 20b McGarrigle E, Galan M, Balmond E. Synlett 2013; 24: 2335
      Article in Thieme Connect
    • 20c Nguyen H, Zhu D, Li X, Zhu J. Angew. Chem. Int. Ed. 2016; 55: 4767
      CrossrefPubMed
  • 21 Leng W, Yao H, He J, Liu X. Acc. Chem. Res. 2018; 51: 628
    CrossrefPubMed
  • 22 Crich D. Acc. Chem. Res. 2010; 43: 1144
    CrossrefPubMed
    • 23a Hasty SJ, Kleine MA, Demchenko AV. Angew. Chem. Int. Ed. 2011; 50: 4197
      CrossrefPubMed
    • 23b Huang W, Zhou Y.-Y, Pan X.-L, Zhou X.-Y, Lei J.-C, Liu D.-M, Chu Y, Yang J.-S. J. Am. Chem. Soc. 2018; 140: 3574
      CrossrefPubMed
    • 23c Zhuo M.-H, Wilbur DJ, Kwan EE, Bennett CS. J. Am. Chem. Soc. 2019; 141: 16743
      CrossrefPubMed
    • 24a Angew. Chem. Int. Ed. 1980; 19: 731
      Crossref
    • 24b Zhu X, Schmidt RR. Angew. Chem. Int. Ed. 2009; 48: 1900
      CrossrefPubMed
  • 25 Li Y, Yang Y, Yu B. Tetrahedron Lett. 2008; 49: 3604
    Crossref
    • 26a Goti G. ChemCatChem 2022; 14: e202200290
      CrossrefPubMed
    • 26b Yao H, Zhang S, Leng W.-L, Leow M.-L, Xiang S, He J, Liao H, Hoang KL. M, Liu X.-W. ACS Catal. 2017; 7: 5456
      Crossref
    • 27a Ciment DM, Ferrier RJ. J. Chem. Soc. C 1966; 441
      Crossref
    • 27b Jose V, Diana EJ, Kanchana US, Mathew TV. J. Organomet. Chem. 2023; 991: 122691
      Crossref
  • 28 Izumi S, Kobayashi Y, Takemoto Y. Angew. Chem. Int. Ed. 2020; 59: 14054
    CrossrefPubMed
    • 29a Deng L, Wang Y, Xu S, Shen A, Zhu H, Zhang S, Zhang X, Niu D. Science 2023; 382: 928
      CrossrefPubMed
    • 29b McKay MJ, Nguyen HM. ACS Catal. 2012; 2: 1563
      CrossrefPubMed
  • 30 Kim H, Men H, Lee C. J. Am. Chem. Soc. 2004; 126: 1336
    CrossrefPubMed
  • 31 Xiong D, Zhang L, Ye X. Org. Lett. 2009; 11
  • 32 Xiang S, Hoang KL. M, He J, Tan YJ, Liu X.-W. Angew. Chem. Int. Ed. 2014; 54: 604
    CrossrefPubMed
  • 33 Palo-Nieto C, Sau A, Galan MC. J. Am. Chem. Soc. 2017; 139: 14041
    CrossrefPubMed
  • 34 Zeng M, Yu C, Wang Y, Wang J, Wang J, Liu H. Angew. Chem. Int. Ed. 2023; 62: e202300424
    CrossrefPubMed
  • 35 Liu B, Liu D, Rong X, Lu X, Fu Y, Liu Q. Angew. Chem. Int. Ed. 2023; 62: e202218544
    CrossrefPubMed
  • 36 Wang Q, Lai M, Luo H, Ren K, Wang J, Huang N, Deng Z, Zou K, Yao H. Org. Lett. 2022; 24: 1587
    CrossrefPubMed
  • 37 Hou M, Xiang Y, Gao J, Zhang J, Wang N, Shi H, Huang N, Yao H. Org. Lett. 2023; 25: 832
    CrossrefPubMed
  • 38 Zhao X, Zhang Z, Xu J, Wang N, Huang N, Yao H. J. Org. Chem. 2023; 88: 11735
    CrossrefPubMed
    • 39a Scott NW. J, Ford MJ, Husbands DR, Whitwood AC, Fairlamb IJ. S. Organometallics 2021; 40: 2995
      CrossrefPubMed
    • 39b Schoenebeck F, Colacot TJ. J. Am. Chem. Soc. 2017; 139: 5194
      CrossrefPubMed
    • 40a Sirirungruang S, Barnum CR, Tang SN, Shih PM. Nat. Prod. Rep. 2023; 40: 1170
      CrossrefPubMed
    • 40b Lv W, Chen Y, Wen S, Ba D, Cheng G. J. Am. Chem. Soc. 2020; 142: 14864
      CrossrefPubMed
    • 40c Xie R, Xu J, Shi H, Xiao C, Wang N, Huang N, Yao H. Org. Lett. 2024; 26: 5162
      CrossrefPubMed
  • 41 Lai M, Othman KA, Yao H, Wang Q, Feng Y, Huang N, Liu M, Zou K. Org. Lett. 2020; 22: 1144
    CrossrefPubMed
  • 42 Ding W.-Y, Liu H.-H, Cheng JK, Yao H, Xiang S.-H, Tan B. Org. Chem. Front. 2022; 9: 6149
    Crossref
  • 43 Wang J, Feng Y, Wang N, Huang N, Yao H. Chin. J. Org. Chem. 2023; 43: 3216
    Crossref
  • 44 Zhang L, Qi K, Xu J, Xing Y, Wang X, Tong L, He Z, Xu W, Li X, Jiang Y. J. Med. Chem. 2023; 66: 4150
    CrossrefPubMed
  • 45 Kobayashi Y, Nakatsuji Y, Li S, Tsuzuki S, Takemoto Y. Angew. Chem. Int. Ed. 2018; 57: 3646
    CrossrefPubMed
  • 46 Wang Y, Yao H, Hua M, Jiao Y, He H, Liu M, Huang N, Zou K. J. Org. Chem. 2020; 85: 7485
    CrossrefPubMed
  • 47 Gao J, Li Y, Wang N, Li Z, Huang N, Yao H. Adv. Synth. Catal. 2023; 365: 2350
    Crossref
  • 48 Li J, Wang M, Jiang X. Org. Lett. 2021; 23: 9053
    CrossrefPubMed
  • 49 Liu Y, Jiao Y, Luo H, Huang N, Lai M, Zou K, Yao H. ACS Catal. 2021; 11: 5287
    Crossref
  • 50 Wang Y, Cao Z, Wang N, Liu M, Zhou H, Wang L, Huang N, Yao H. Adv. Synth. Catal. 2023; 365: 1699
    Crossref
    • 51a Comely AC, Eelkema R, Minnaard AJ, Feringa BL. J. Am. Chem. Soc. 2003; 125: 8714
      CrossrefPubMed
    • 51b Babu RS, O’Doherty GA. J. Am. Chem. Soc. 2003; 125: 12406
      CrossrefPubMed