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DOI: 10.1055/s-0042-1752404
Improved Total Synthesis of 1,3,6-Trigalloyl-β-d-glucose from Glucose
This work was supported by Natural Sciences and Engineering Research Council of Canada (NSERC) under the Discovery Grant Program (RGPIN-2019-06113) (to A. B. C.), the Canada Foundation for Innovation Leaders Opportunity Funds, by the FRQNT Centre in Green Chemistry and Catalysis Strategic Cluster Grant (RS-265155), and by the Université de Montréal.
This paper is dedicated to the memory of Prof. David A. Evans for his unparalleled mentorship and outstanding scientific contributions.
Abstract
A total synthesis of the naturally occurring 1,3,6-trigalloyl-β-d-glucose is reported. The highlights of the synthesis include a regioselective benzylation of levoglucosan, followed by a 1,6-ring opening via acetolysis. Galloyl substituents were introduced via esterification, and the mixture of anomers obtained could be fully converted into the targeted β-anomer via selective hydrazinolysis followed by activation of the anomeric position by a trichloroacetimidate of the 1′-anomeric hydroxyl group. 1,3,6-Trigalloyl-β-d-glucose and its synthetic α-anomer were obtained in an overall yield of 31% and 22%, respectively, from levoglucosan or in an overall yield of 37% of the β-isomer exclusively by recycling the α-isomer.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0042-1752404.
- Supporting Information
Publication History
Received: 13 November 2022
Accepted after revision: 22 January 2023
Article published online:
27 February 2023
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References
- 1 Present address: Department of Chemistry, Université du Québec à Montréal, P. O. Box 888 Station Downtown, Montréal, Québec H3C 3P8, Canada
- 2 Schmidt OT, Demmler K, Bittermann H, Stephan P. Justus Liebigs Ann. Chem. 1957; 609: 192
- 3 Gaudreault R, van de Ven TG. M, Whitehead MA. J. Mol. Model. 2002; 8: 73
- 4 Binette V, Côté S, Haddad M, Nguyen PT, Bélanger S, Bourgault S, Ramassamy C, Gaudreault R, Mousseau N. Phys. Chem. Chem. Phys. 2021; 23: 14873
- 5 Haddad M, Gaudreault R, Sasseville G, Nguyen PT, Wiebe H, Ven TV, Bourgault S, Mousseau N, Ramassamy C. Int. J. Mol. Sci. 2022; 23: 2643
- 6 Lee SH, Jun M, Choi JY, Yang EJ, Hur JM, Bae K, Seong YH, Huh TL, Song KS. Arch. Pharm. Res. 2007; 30: 827
- 7 Sylla T, Pouységu L, Da Costa G, Deffieux D, Monti JP, Quideau S. Angew. Chem. Int. Ed. 2015; 54: 8217
- 8 Li CW, Dong HJ, Cui CB. Molecules 2015; 20: 2034
- 9 Breijyeh Z, Karaman R. Molecules 2020; 25: 5789
- 10 Gaudreault R, Mousseau N. Curr. Alzheimer Res. 2019; 16: 529
- 11 Schmidt OT, Schulz J, Fiesser H. Justus Liebigs Ann. Chem. 1967; 706: 187
- 12 Tanaka T, Fukumori M, Ochi T, Kouno I. J. Nat. Prod. 2003; 66: 759
- 13 Schmidt OT, Klinger G. Justus Liebigs Ann. Chem. 1957; 609: 199
- 14 Denavit V, Lainé D, St-Gelais J, Johnson PA, Giguère D. Nat. Commun. 2018; 9: 4721
- 15 Zottola MA, Alonso R, Vite GD, Fraser-Reid B. J. Org. Chem. 1989; 54: 6123
- 16 Iversen T, Bundle DR. Can. J. Chem. 1982; 60: 299
- 17a Nakazono M, Ma L, Zaitsu K. Tetrahedron Lett. 2002; 43: 8185
- 17b Das M, Senapati K, Panda SS, Bhattacharya P, Jana S, Mandal SM, Basak A. RSC Adv. 2016; 6: 85254
- 17c Ren YL, Himmeldirk K, Chen XZ. J. Med. Chem. 2006; 49: 2829
- 18 Fletcher S, Gunning PT. Tetrahedron Lett. 2008; 49: 4817
- 19 Gigg R, Warren CD. J. Chem. Soc. C 1968; 1903
- 20 Hazelard D, Compain P. Eur. J. Org. Chem. 2021; 3501
- 21 CCDC 2219347 (14) and 2219346 (15) contain the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/structures
- 22 Spencer CM, Cai Y, Martin R, Lilley TH, Haslam E. J. Chem. Soc., Perkin Trans. 2 1990; 651
- 23 Excoffier G, Gagnaire D, Utille JP. Carbohydr. Res. 1975; 39: 368