Photo-Induced Glycosylations Using Organophotoacids: A New Environmentally Benign Carbohydrate Synthesis

Abstract

This account reports the glycosylation reactions of glycosyl trichloroacetimidates and various alcohols using several organophotoacids as activators under photo-irradiation conditions. The reactions proceed smoothly to give the corresponding glycosides in high yields. The organophotoacids can be recovered and reused many times without any loss of efficiency, which demonstrates their environmentally benign features.

1 Introduction

2 Photo-Induced Glycosylation Using Naphthol Derivatives

3 Photo-Induced Glycosylation Using Aryl Thioureas

4 Photo-Induced Glycosylation Using Diaryldisulfides

5 Photo-Induced Glycosylation Using Diarylthiophenes

6 Conclusion

Key words

carbohydrates - glycosylation - photoreaction - organophotoacids - environmentally benign

Publication History

Received: 12 May 2023

Accepted after revision: 19 June 2023

Article published online:
21 July 2023

• References

• 1a Carbohydrates in Chemistry and Biology, Vols. 1–4. Ernst B, Hart GW, Sinaÿ P. Wiley-VCH; Weinheim: 2000
• 1b Glycoscience, Chemistry and Chemical Biology, Vols. 1-3. Fraser-Reid BO, Tatsuta K, Thiem J. Springer; Berlin: 2001
• 2 Functional Food Carbohydrates . Biliaderis CG, Izydorczyck MS. CRC Press; Boca Raton: 2006
• 3a Toshima K, Tatsuta K. Chem. Rev. 1993; 93: 1503
• 3b Toshima K, Sasaki K. In Comprehensive Glycoscience . Karmerling JP, Boons G.-J, Lee YC, Suzuki A, Taniguchi N, Voragen AG. J. Elsevier; Oxford 2007; 261–3: 11
• 3c Demchenko AV. In Handbook of Chemical Glycosylation: Advances in Stereoselectivity and Therapeutic Relevance. Demchenko AV. Wiley-VCH; Weinheim: 2008: 1-27

For selected examples, see:
• 4a Furuta T, Takeuchi K, Iwamura M. Chem. Commun. 1996; 157
• 4b Cumpstey I, Crich D. J. Carbohydr. Chem. 2011; 30: 469
• 4c Wever WJ, Cinelli MA, Bowers AA. Org. Lett. 2013; 15: 30
• 4d Nakanishi M, Takahashi D, Toshima K. Org. Biomol. Chem. 2013; 11: 5079

For selected examples, see:
• 5a Andrews RS, Becker JJ, Gagné MR. Angew. Chem. Int. Ed. 2010; 49: 7274
• 5b Andrews RS, Becker JJ, Gagné MR. Org. Lett. 2011; 13: 2406
• 5c Andrews RS, Becker JJ, Gagné MR. Angew. Chem. Int. Ed. 2012; 51: 4140
• 6 Tolbert LM, Solntsev KM. Acc. Chem. Res. 2002; 35: 19
• 7 Nishikubo Y, Kanzaki S, Matsumura S, Toshima K. Tetrahedron. Lett. 2006; 47: 8125
• 8a Schmidt RR, Michael J. Angew. Chem. Int. Ed. 1980; 19: 731
• 8b Schmidt RR. Angew. Chem. Int. Ed. 1986; 25: 212
• 9 Bartok W, Hartman R, Lucchesi P. Photochem. Photobiol. 1965; 4: 499
• 10 Tolbert LM, Haubrich JE. J. Am. Chem. Soc. 1994; 116: 10593
• 11 A Blak-Ray (B-100A) purchased from UVP, Inc. was used.
• 12 A radiometer sensor (UVX-36) purchased from UVP, Inc. was used. UV light at 12 mW/cm² was obtained using one lamp placed at 5 cm from the reaction mixture.
• 13 It was confirmed that other acid-sensitive glycosyl donors, such as the corresponding glycal or glycosyl diethyl phosphite, could not effectively be activated by the organophotoacids used.
• 14 Iwata R, Uda K, Takahashi D, Toshima K. Chem. Commun. 2014; 50: 10695

For a selected review, see:
• 15a Fang X, Wang C.-J. Chem. Commun. 2015; 51: 1185 For selected examples, see
• 15b Okino T, Hoashi Y, Takemoto Y. J. Am. Chem. Soc. 2003; 125: 12672
• 15c Wittkopp A, Schreiner PR. Chem. Eur. J. 2003; 9: 407
• 15d Okino T, Hoashi Y, Furukawa T, Xu X, Takemoto Y. J. Am. Chem. Soc. 2005; 127: 119
• 15e Herrera RP, Sgarzani V, Bernardi L, Ricci A. Angew. Chem. Int. Ed. 2005; 44: 6576
• 15f Cao C.-L, Ye M.-C, Sun X.-L, Tang Y. Org. Lett. 2006; 8: 2901
• 15g Xu H, Zuend SJ, Woll MP, Tao Y, Jacobsen EN. Science 2010; 327: 986
• 15h Zhang Z, Lippert KM, Hausmann H, Kotke M, Schreiner PR. J. Org. Chem. 2011; 76: 9764
• 15i Lin S, Jacobsen EN. Nat. Chem. 2012; 4: 817
• 16a Vallavoju N, Selvakumar S, Jockusch S, Sibi MP, Sivaguru J. Angew. Chem. Int. Ed. 2014; 53: 5604
• 16b Telmesani R, Park SH, Lynch-Colameta T, Beeler AB. Angew. Chem. Int. Ed. 2015; 54: 11521
• 17 Balmond EI, Coe DM, Galan MC, McGarrigle EM. Angew. Chem. Int. Ed. 2012; 51: 9152
• 18a Li Q, Levi SM, Wagen CC, Wendlandt AE, Jacobsen EN. Nature 2022; 608: 74
• 18b Li Q, Levi SM, Jacobsen EN. J. Am. Chem. Soc. 2020; 142: 11865
• 18c Mayfield AB, Metternich JB, Trotta AH, Jacobsen EN. J. Am. Chem. Soc. 2020; 142: 4061
• 18d Levi SM, Jacobsen EN. Org. React. 2019; 100: 801
• 18e Levi SM, Li Q, Roetheli AR, Jacobsen EN. Proc. Natl. Acad. Sci. U. S. A. 2019; 116: 35
• 18f Park Y, Harper KC, Kuhl N, Kwan E. E., Liu R. Y., Jacobsen E. N. 2017; 355: 162
• 19a Li X, Deng H, Luo S, Cheng J.-P. Eur. J. Org. Chem. 2008; 4350
• 19b Jakab G, Tancon C, Zhang Z, Lippert KM, Schreiner PR. Org. Lett. 2012; 14: 1724
• 20 Geng Y, Kumar A, Faidallah HM, Albar HA, Mhkalid IA, Schmidt RR. Angew. Chem. Int. Ed. 2013; 52: 10089
• 21 Demchenko AV. Synlett 2003; 1225
• 22 Hashimoto S, Hayashi M, Noyori R. Tetrahedron Lett. 1984; 25: 1379
• 23 Kimura T, Eto T, Takahashi D, Toshima K. Org. Lett. 2016; 18: 3190

After the publication of our work, photo-induced glycosylations using eosin Y as an organo Brønsted photoacid were reported, see:
• 24a Zhao G, Wang T. Angew. Chem. Int. Ed. 2018; 57: 6120
• 24b Liu J, Yin S, Wang H, Li H, Ni G. Carbohydr. Res. 2020; 490: 107963
• 24c Zhao G, Li J, Wang T. Chem. Commun. 2021; 57: 12659
• 25 Henrich JD, Suchyta S, Kohler B. J. Phys. Chem. B 2015; 119: 2737
• 26 Craig DP, Ross IG. J. Chem. Soc. 1954; 1589
• 27a Suzuki K, Maeta H, Matsumoto T. Tetrahedron Lett. 1989; 30: 6879
• 27b Suzuki K, Maeta H, Matsumoto T, Tsuchihashi G. Tetrahedron Lett. 1988; 29: 3571
• 27c Matsumoto T, Maeta H, Suzuki K, Tsuchihashi G. Tetrahedron Lett. 1988; 29: 3567
• 28 Iibuchi N, Eto T, Aoyagi M, Kurinami R, Sakai H, Hasobe T, Takahashi D, Toshima K. Org. Biomol. Chem. 2020; 18: 851
• 29 Otani N, Higashiyama K, Sakai H, Hasobe T, Takahashi D, Toshima K. Eur. J. Org. Chem. 2023; 26: e202300287