Jump to ContentJump to Main Navigation
Show Summary Details
More options …

Pure and Applied Chemistry

The Scientific Journal of IUPAC

Ed. by Burrows, Hugh / Stohner, Jürgen

IMPACT FACTOR 2018: 2.350
5-year IMPACT FACTOR: 4.037

CiteScore 2018: 4.66

SCImago Journal Rank (SJR) 2018: 1.240
Source Normalized Impact per Paper (SNIP) 2018: 1.826

See all formats and pricing
More options …
Volume 91, Issue 7


Stereoselective synthesis of sugar mimetics from simple monosaccharides

Sławomir Jarosz
  • Corresponding author
  • Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland
  • Email
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
/ Karolina Tiara
  • Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
/ Mykhaylo A. Potopnyk
  • Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
Published Online: 2019-04-05 | DOI: https://doi.org/10.1515/pac-2019-0116


A number of bicyclic imino- and carba-sugars (examples are presented in the Scheme) can be obtained from simple monosaccharides (hexoses or pentoses) by various methods.

Keywords: carbasugar; ICS-29; iminosugar; stereoselective synthesis

Article note

A collection of invited papers based on presentations at the 29th International Carbohydrate Symposium (ICS-29), held in the University of Lisbon, Portugal, 14–19 July 2018.


  • [1]

    M. Bols. Acc. Chem. Res. 31, 1 (1998).Google Scholar

  • [2]

    L. Cipolla, F. Peri, B. La Ferla, C. Redaelli, F. Nicotra. Curr. Org. Synth. 2, 153 (2005).CrossrefGoogle Scholar

  • [3]

    G. Horne, F. X. Wilson, J. Tinsley, D. H. Williams, R. Storer. Drug Discov. Today 16, 107 (2011).CrossrefGoogle Scholar

  • [4]

    A. E. Stütz (Ed.) Iminosugars as Glycosidases Inhibitors: Norjirmycin and Beyond. Wiley-VCH, Weinheim (1999).Google Scholar

  • [5]

    P. Compain, O. R. Martin (Eds.) Iminosugars: From Synthesis to Therapeutic Applications. Wiley-VCH, Weinheim (2007).Google Scholar

  • [6]

    B. G. Winchester. Tetrahedron Asymmetr. 20, 645 (2009).CrossrefGoogle Scholar

  • [7]

    P. Compain, V. Chagnault, O. R. Martin. Tetrahedron Asymmetr. 20, 672 (2009).CrossrefGoogle Scholar

  • [8]

    M. Brambilla, S. G. Davies, A. M. Fletcher, J. E. Thomson. Tetrahedron Asymmetr. 25, 387 (2014).CrossrefGoogle Scholar

  • [9]

    B.-C. Qian, A. Kamori, K. Kinami, A. Kato, Y.-X. Li, G. W. J. Fleet, C.-Y. Yu. Org. Biomol. Chem. 14, 4488 (2016).CrossrefGoogle Scholar

  • [10]

    N. J. Pawar, S. V. Parihar, A. Khan, R. Joshi, D. D. J. Dhavale. J. Med. Chem. 58, 7820 (2015).CrossrefGoogle Scholar

  • [11]

    I. Robina, A. J. Moreno-Vargas, A. T. Carmona, P. Vogel. Curr. Drug Metab. 5, 329 (2004).CrossrefGoogle Scholar

  • [12]

    Y. Chapleur (Ed.) Carbohydrate Mimics. Concepts and Methods. Wiley, Weinheim (1998).Google Scholar

  • [13]

    O. Arjona, A. M. Gómez, J. C. López, J. Plumet. Chem. Rev. 107, 1919 (2007).CrossrefGoogle Scholar

  • [14]

    Y. Kobayashi. “Carbasugars: synthesis and functions”, in Glycoscience: Chemistry and Chemical Biology, 2nd ed. B. O. Frazer-Reid, K. Tatsuta, J. Thiem (Eds.), p. 1913, Springer-Verlag, Berlin, Heidelberg, New York (2001).Google Scholar

  • [15]

    H. Kumamoto, M. Fukano, T. Nakano, K. Iwagami, C. Takeyama, S. Kohgo, S. Imoto, M. Amano, N. Kuwata-Higashi, M. Aoki, H. Abe, H. Mitsuya, K. Fukuhara, K. Haraguchi. J. Org. Chem. 81, 2827 (2016).CrossrefGoogle Scholar

  • [16]

    G. Witkowski, M. Kowalski, Ł. Szyszka, M. A. Potopnyk, S. Jarosz. Tetrahedron Asymmetr. 27, 747 (2016).CrossrefGoogle Scholar

  • [17]

    G. Mehta, S. S. Ramesh. Chem. Commun. 2429 (2000).Google Scholar

  • [18]

    J. P. Michael. Nat. Prod. Rep. 15, 571 (1998).CrossrefGoogle Scholar

  • [19]

    P. Herczegh, I. Kovács, L. Szilágyi, F. Sztaricskai, A. Berecibar, C. Riche, A. Chiaroni, A. Olesker, G. Lukacs. Tetrahedron 51, 2969 (1995).CrossrefGoogle Scholar

  • [20]

    W. H. Pearson, E. J. Hembre. J. Org. Chem. 61, 5537 (1996).CrossrefGoogle Scholar

  • [21]

    S. Jarosz. Curr. Org. Chem. 12, 985 (2008).CrossrefGoogle Scholar

  • [22]

    S. Jarosz, M. Nowogrodzki, M. Magdycz, M. A. Potopnyk. Carbohydr. Chem. 37, 303 (2011).CrossrefGoogle Scholar

  • [23]

    M. A. Potopnyk, P. Cmoch, M. Cieplak, A. Gajewska, S. Jarosz. Tetrahedron Asymmetr. 22, 780 (2011).CrossrefGoogle Scholar

  • [24]

    S. Jarosz, B. Fraser-Reid. J. Org. Chem. 54, 4011 (1989).CrossrefGoogle Scholar

  • [25]

    S. Jarosz. Tetrahedron 53, 10765 (1997).CrossrefGoogle Scholar

  • [26]

    S. Jarosz, A. Gaweł. Eur. J. Org. Chem. 3415 (2005).Google Scholar

  • [27]

    M. Magdycz, S. Jarosz. Tetrahedron Asymmetr. 24, 1402 (2013).CrossrefGoogle Scholar

  • [28]

    S. Jarosz. J. Chem. Soc. Perkin Trans. I. 3579 (1997).Google Scholar

  • [29]

    M. Magdycz, P. Cmoch, S. Jarosz. Heterocycles 46, 1303 (2010).Google Scholar

  • [30]

    M. Magdycz, S. Jarosz. Tetrahedron Asymmetr. 24, 1412 (2013).CrossrefGoogle Scholar

  • [31]

    P. Herczegh, M. Zsély, L. Szilágyi, I. Bajza, A. Kovács, G. Batta, R. Bognár. Cycloaddition React in Carbohydrate Chem 494, 112 (1992).Google Scholar

  • [32]

    G. Witkowski, S. Jarosz. Synlett 24, 1813 (2013).CrossrefGoogle Scholar

  • [33]

    M. Malik, S. Jarosz. Beilstein J. Org. Chem. 12, 2602 (2016).CrossrefGoogle Scholar

  • [34]

    M. Malik, P. Cmoch, M. A. Potopnyk, S. Jarosz. Tetrahedron Asymmetr. 28, 1750 (2017).CrossrefGoogle Scholar

  • [35]

    M. Malik, G. Witkowski, M. Ceborska, S. Jarosz. Org. Lett. 15, 6214 (2013).CrossrefGoogle Scholar

  • [36]

    K. J. Fraunhoffer, N. Prabagaran, L. E. Sirois, M. C. White, J. Am. Chem. Soc. 128, 9032 (2006).CrossrefGoogle Scholar

  • [37]

    P. E. Gormisky, M. C. White. J. Am. Chem. Soc. 133, 12584 (2011).CrossrefGoogle Scholar

  • [38]

    M. Malik, G. Witkowski, S. Jarosz. Org. Lett. 16, 3816 (2014).CrossrefGoogle Scholar

  • [39]

    M. Malik, S. Jarosz. Carbohydr. Chem. 42, 313 (2017).Google Scholar

  • [40]

    L. Miesch, T. Welsch, L. Toupet. Synthesis 161 (2011).Google Scholar

  • [41]

    M. Malik, S. Jarosz. Org. Biomol. Chem. 14, 1764 (2016).CrossrefGoogle Scholar

  • [42]

    M. Mondon, N. Fontelle, J. Dásiré, F. Lecornué, J. Guillard, J. Marrot, Y. Blériot. Org. Lett. 14, 870 (2012).CrossrefGoogle Scholar

  • [43]

    S. S. Prasad, N. R. Reddy, S. Baskaran. J. Org. Chem. 83, 9604 (2018).CrossrefGoogle Scholar

  • [44]

    S. Senthilkumar, S. S. Prasad, P. S. Kumar, S. Baskaran. Chem. Commun. 50, 1549 (2014).CrossrefGoogle Scholar

  • [45]

    S. Senthilkumar, S. S. Prasad, A. Das, S. Baskaran. Chem. Eur. J. 21, 15914 (2015).CrossrefGoogle Scholar

  • [46]

    K. Chinthapally, R. Karthik, S. Senthilkumar, S. Baskaran. Chem. Eur. J. 23, 533 (2017).CrossrefGoogle Scholar

  • [47]

    S. S. Prasad, S. Senthilkumar, A. Srivastava, S. Baskaran. Org. Lett. 19, 4403 (2017).CrossrefGoogle Scholar

  • [48]

    S. S. Prasad, S. Baskaran. J. Org. Chem. 83, 1558 (2018).CrossrefGoogle Scholar

  • [49]

    Q. Shen, J. Shao, Q. Peng, W. Zhang, L. Ma, A. S. C. Chan, L. Gu. J. Med. Chem. 53, 8252 (2010).CrossrefGoogle Scholar

  • [50]

    S. Tangara, C. Aupic, A. Kanazawa, J. F. Poisson, S. Py. Org. Lett. 19, 4842 (2017).CrossrefGoogle Scholar

  • [51]

    S. Tangara, A. Kanazawa, S. Py. Eur. J. Org. Chem. 6357 (2017).Google Scholar

About the article

Published Online: 2019-04-05

Published in Print: 2019-07-26

Citation Information: Pure and Applied Chemistry, Volume 91, Issue 7, Pages 1137–1148, ISSN (Online) 1365-3075, ISSN (Print) 0033-4545, DOI: https://doi.org/10.1515/pac-2019-0116.

Export Citation

©2019 IUPAC & De Gruyter. This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License. For more information, please visit: http://creativecommons.org/licenses/by-nc-nd/4.0/.Get Permission

Citing Articles

Here you can find all Crossref-listed publications in which this article is cited. If you would like to receive automatic email messages as soon as this article is cited in other publications, simply activate the “Citation Alert” on the top of this page.

Quentin Foucart, Yuna Shimadate, Jérôme Marrot, Atsushi Kato, Jérôme Désiré, and Yves Blériot
Organic & Biomolecular Chemistry, 2019, Volume 17, Number 30, Page 7204

Comments (0)

Please log in or register to comment.
Log in