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

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

Publikationsverlauf

Eingereicht: 30. April 2024

Angenommen nach Revision: 18. Juni 2024

Accepted Manuscript online:
19. Juni 2024

Artikel online veröffentlicht:
10. Juli 2024

• References

• 1a Crawford CJ, Seeberger PH. Chem. Soc. Rev. 2023; 52: 7773
• 1b Dey S, Lo H.-J, Wong C.-H. J. Am. Chem. Soc. 2019; 141: 10309
• 1c Flitsch SL. Chem. Rev. 2022; 122: 15501
• 1d Kapoor VK, Kaur A. Mini-Rev. Med. Chem. 2013; 13: 584
• 2a Huang W, Fan S, Gao J, Luo S, Tang S, Liu J, Wang X. Angew. Chem. Int. Ed. 2022; 61: e202204907
• 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
• 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
• 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
• 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
• 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
• 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
• 5a Kumavath R, Paul S, Pavithran H, Paul MK, Ghosh P, Barh D, Azevedo V. Biomolecules 2021; 11: 1275
• 5b Prassas I, Diamandis EP. Nat. Rev. Drug Discov. 2008; 7: 926
• 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
• 5d Grynkiewicz G, Szeja W. J. Mol. Biomark. Diagn. 2015; 6: 100259
• 5e Škubník J, Bejček J, Pavlíčková VS, Rimpelová S. Molecules 2021; 26: 5627
• 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
• 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
• 7 Abdel-Sattar E, Ali DE. Rev. Bras. Farmacogn. 2022; 32: 188
• 8a Allard B, Allard D, Buisseret L, Stagg J. Nat. Rev. Clin. Oncol. 2020; 17: 611
• 8b Stirrups R. Lancet Oncol. 2019; 20: e402
• 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
• 10b Chang C, Ho Y, Lin S, Liu H. J. Diabetes Mellitus 2019; 9: 77
• 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
• 11 Roy R, Banerjee K, Bhattacharya R, Mukhopadhyay A. Ann. Oncol. 2016; 27: ix49
• 12 Raninga P, Lee A, Sinha D, Shin Y.-Y, Mittal D, Kalimutho M, Khanna KK. Ann. Oncol. 2019; 30: v3
• 13 Zhao Q, Wang M, Xu D, Zhang Q, Liu W. Nature 2015; 518: 115
• 14a David RFriend, Chang GW. J. Med. Chem. 1985; 28: 51
• 14b Louveau T, Osbourn A. Cold Spring Harbor Perspect. Biol. 2019; 11: a034744
• 14c Chen F, Huang G. Eur. J. Med. Chem. 2019; 182: 111612
• 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
• 15b Wang J, Zhang Y, Zhu Y, Liu J, Chen Y, Cao X, Yang Y. Org. Lett. 2020; 22: 8780
• 16 Bennett CS, Galan MC. Chem. Rev. 2018; 118: 7931
• 17a Babu RS, Chen Q, Kang S.-W, Zhou M, O’Doherty GA. J. Am. Chem. Soc. 2012; 134: 11952
• 17b Zhang Y, Wang L, Zhou Q, Li Z, Li D, Yin C, Wang X, Xiao G. Angew. Chem. Int. Ed. 2023; 62: e202301351
• 18a Desai SP, Yatzoglou G, Turner JA, Taylor MS. J. Am. Chem. Soc. 2024; 146: 4973
• 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
• 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
• 20a Demkiw KM, Remmerswaal WA, Hansen T, van der Marel GA, Codée JD. C, Woerpel KA. Angew. Chem. Int. Ed. 2022; 61: e202209401
• 20b McGarrigle E, Galan M, Balmond E. Synlett 2013; 24: 2335
• 20c Nguyen H, Zhu D, Li X, Zhu J. Angew. Chem. Int. Ed. 2016; 55: 4767
• 21 Leng W, Yao H, He J, Liu X. Acc. Chem. Res. 2018; 51: 628
• 22 Crich D. Acc. Chem. Res. 2010; 43: 1144
• 23a Hasty SJ, Kleine MA, Demchenko AV. Angew. Chem. Int. Ed. 2011; 50: 4197
• 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
• 23c Zhuo M.-H, Wilbur DJ, Kwan EE, Bennett CS. J. Am. Chem. Soc. 2019; 141: 16743
• 24a Angew. Chem. Int. Ed. 1980; 19: 731
• 24b Zhu X, Schmidt RR. Angew. Chem. Int. Ed. 2009; 48: 1900
• 25 Li Y, Yang Y, Yu B. Tetrahedron Lett. 2008; 49: 3604
• 26a Goti G. ChemCatChem 2022; 14: e202200290
• 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
• 27a Ciment DM, Ferrier RJ. J. Chem. Soc. C 1966; 441
• 27b Jose V, Diana EJ, Kanchana US, Mathew TV. J. Organomet. Chem. 2023; 991: 122691
• 28 Izumi S, Kobayashi Y, Takemoto Y. Angew. Chem. Int. Ed. 2020; 59: 14054
• 29a Deng L, Wang Y, Xu S, Shen A, Zhu H, Zhang S, Zhang X, Niu D. Science 2023; 382: 928
• 29b McKay MJ, Nguyen HM. ACS Catal. 2012; 2: 1563
• 30 Kim H, Men H, Lee C. J. Am. Chem. Soc. 2004; 126: 1336
• 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
• 33 Palo-Nieto C, Sau A, Galan MC. J. Am. Chem. Soc. 2017; 139: 14041
• 34 Zeng M, Yu C, Wang Y, Wang J, Wang J, Liu H. Angew. Chem. Int. Ed. 2023; 62: e202300424
• 35 Liu B, Liu D, Rong X, Lu X, Fu Y, Liu Q. Angew. Chem. Int. Ed. 2023; 62: e202218544
• 36 Wang Q, Lai M, Luo H, Ren K, Wang J, Huang N, Deng Z, Zou K, Yao H. Org. Lett. 2022; 24: 1587
• 37 Hou M, Xiang Y, Gao J, Zhang J, Wang N, Shi H, Huang N, Yao H. Org. Lett. 2023; 25: 832
• 38 Zhao X, Zhang Z, Xu J, Wang N, Huang N, Yao H. J. Org. Chem. 2023; 88: 11735
• 39a Scott NW. J, Ford MJ, Husbands DR, Whitwood AC, Fairlamb IJ. S. Organometallics 2021; 40: 2995
• 39b Schoenebeck F, Colacot TJ. J. Am. Chem. Soc. 2017; 139: 5194
• 40a Sirirungruang S, Barnum CR, Tang SN, Shih PM. Nat. Prod. Rep. 2023; 40: 1170
• 40b Lv W, Chen Y, Wen S, Ba D, Cheng G. J. Am. Chem. Soc. 2020; 142: 14864
• 40c Xie R, Xu J, Shi H, Xiao C, Wang N, Huang N, Yao H. Org. Lett. 2024; 26: 5162
• 41 Lai M, Othman KA, Yao H, Wang Q, Feng Y, Huang N, Liu M, Zou K. Org. Lett. 2020; 22: 1144
• 42 Ding W.-Y, Liu H.-H, Cheng JK, Yao H, Xiang S.-H, Tan B. Org. Chem. Front. 2022; 9: 6149
• 43 Wang J, Feng Y, Wang N, Huang N, Yao H. Chin. J. Org. Chem. 2023; 43: 3216
• 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
• 45 Kobayashi Y, Nakatsuji Y, Li S, Tsuzuki S, Takemoto Y. Angew. Chem. Int. Ed. 2018; 57: 3646
• 46 Wang Y, Yao H, Hua M, Jiao Y, He H, Liu M, Huang N, Zou K. J. Org. Chem. 2020; 85: 7485
• 47 Gao J, Li Y, Wang N, Li Z, Huang N, Yao H. Adv. Synth. Catal. 2023; 365: 2350
• 48 Li J, Wang M, Jiang X. Org. Lett. 2021; 23: 9053
• 49 Liu Y, Jiao Y, Luo H, Huang N, Lai M, Zou K, Yao H. ACS Catal. 2021; 11: 5287
• 50 Wang Y, Cao Z, Wang N, Liu M, Zhou H, Wang L, Huang N, Yao H. Adv. Synth. Catal. 2023; 365: 1699
• 51a Comely AC, Eelkema R, Minnaard AJ, Feringa BL. J. Am. Chem. Soc. 2003; 125: 8714
• 51b Babu RS, O’Doherty GA. J. Am. Chem. Soc. 2003; 125: 12406