European Journal of Chemistry

Synthesis of esters derived from 2,3,4,6-tetra-O-acetyl-1-[4-(2-hydroxyethyl)-1H-1,2,3-triazol-1-yl]-β-D-glucopyranose



Main Article Content

Tiago Alexandre Dinis Pinto
Marilia Silva
Silvia Cunha
Ana Maria Ferreira Oliveira-Campos
Ligia Marona Rodrigues
Radim Hrdina
Ana Paula Esteves

Abstract

2,3,4,6-Tetra-o-acetyl-1-[4-(2-hydroxyethyl)-1H-1,2,3-triazol-1-yl]-β-D-glucopyranose was prepared and reacted with several acids, either commercially available or prepared. These included, aliphatic or aromatic acids (phenylacetic acid derivatives, benzoic derivatives), palmitic acid and the protected amino acids N-(benzyloxycarbonyl)glycine and N-(tert-butyloxycarbonyl)-phenylalanine. Two other acids, 2-(3-bromopropoxy)benzoic acid and 2-(5-bromopentoxy)benzoic acid (analogues of salicylic acid were synthesized), whose preparation is also described in this work. The esterification was performed either with N,N'-dicyclohexylcarbodiimide (DCC)/4-dimethylaminopyridine (DMAP) or by reacting the acyl chlorides with the alcohol in the presence of triethylamine. The products were isolated in fair yields and fully characterized by the usual analytical techniques.

4_1_64_69

icon graph This Abstract was viewed 1586 times | icon graph Article PDF downloaded 835 times

How to Cite
(1)
Pinto, T. A. D.; Silva, M.; Cunha, S.; Oliveira-Campos, A. M. F.; Rodrigues, L. M.; Hrdina, R.; Esteves, A. P. Synthesis of Esters Derived from 2,3,4,6-Tetra-O-Acetyl-1-[4-(2-Hydroxyethyl)-1H-1,2,3-Triazol-1-Yl]-β-D-Glucopyranose. Eur. J. Chem. 2013, 4, 64-69.

Article Details

Share
Crossref - Scopus - Google - European PMC
References

[1]. Green, R.; Tocoli, F. E.; Lee, S. H.; Nihe, K-I.; Kubo, I. Eur. J. Med. Chem. 2008, 43, 1315-1320.
http://dx.doi.org/10.1016/j.ejmech.2007.08.012
PMid:17959274

[2]. Djurendic, E.; Vujaskovic, S. D.; Sakac, M.; Ajdukovic, J.; Gakovic, A.; Kojic, V.; Bogdanovic, G.; Klisuric, O.; Gasi, K. P. Arkivoc 2011, 2, 83-102.

[3]. Petrlikova, E.; Waisser, K.; Buchta, V.; Jilek, P.; Vejsova, M. Bioorg. Med. Chem. Lett. 2010, 20, 4535-4538.
http://dx.doi.org/10.1016/j.bmcl.2010.06.023
PMid:20584611

[4]. Gilmer, J. F.; Moriarty, L. M.; Clancy, J. M. Bioorg. Med. Chem. Lett. 2007, 17, 3217-3220.
http://dx.doi.org/10.1016/j.bmcl.2007.03.009
PMid:17376682

[5]. Tang, S.; June, S. M.; Howell, B. A.; Chai, M. Tetrahedron Lett. 2006, 47, 7671-7675.
http://dx.doi.org/10.1016/j.tetlet.2006.08.110

[6]. Davaran, S.; Hanaee, J.; Khosravi, A. J. Control. Release 1999, 58, 279-287.
http://dx.doi.org/10.1016/S0168-3659(98)00167-9

[7]. Erdmann, L.; Macedo, B.; Uhrich, K. E. Biomaterials 2000, 21, 2507-2512.
http://dx.doi.org/10.1016/S0142-9612(00)00118-6

[8]. Marwan, A. G.; Nagel, C. W. J. Food Science 1986, 51, 1069-1070
http://dx.doi.org/10.1111/j.1365-2621.1986.tb11236.x

[9]. Lazzarato, L.; Donnola, M.; Rolando, B.; Chegaev, K.; Marini, E.; Cena, C.; Di Stilo, A.; Fruttero, R.; Biondi, S.; Ongini, E.; Gasco, A. J. Med. Chem. 2009, 52, 5058-5068.
http://dx.doi.org/10.1021/jm900587h
PMid:20560642

[10]. DeLuca, D.; di Nino, A.; Liguori, A.; Procopio, A.; Sindona, G. Lipids 1997, 32, 559-563
http://dx.doi.org/10.1007/s11745-997-0071-7

[11]. Bottcher, C.; Spengler, J.; Essawy, S. A.; Burger, K. Monatsh. Chem. 2004, 135, 853-863.

[12]. Danishefsky, S. J.; Allen, J. R. Angew. Chem., Int. Ed. 2000, 39, 836-863.
http://dx.doi.org/10.1002/(SICI)1521-3773(20000303)39:5<836::AID-ANIE836>3.0.CO;2-I

[13]. Lohof, E.; Planker, E.; Mang, C.; Burkhart, F.; Dechantsreiter, M. A.; Haubner, R.; Wester, H. J.; Schwaiger, M.; Holzemann, G.; Goodman, S. L.; Kessler, H. Angew. Chem., Int. Ed. 2000, 39, 2761-2764.
http://dx.doi.org/10.1002/1521-3773 (20000804)39:15<2761::AID-ANIE2761>3.0.CO;2-9

[14]. Coutrot, F.; Grison, C.; Coutrot, P. C. R. Chimie 2004, 7, 3-13.
http://dx.doi.org/10.1016/j.crci.2003.07.016

[15]. Davis, B. G. Chem. Rev. 2002, 102, 579-602.
http://dx.doi.org/10.1021/cr0004310
PMid:11841255

[16]. Meinjohanns, E.; Meldal, M.; Paulsen, H.; Dwek, R. A.; Bock, K. J. Chem. Soc., Perkin Trans. 1 1998, 549-560.

[17]. Tarasenko, O.; Islam, S.; Paquiot, D.; Levon, K. Carbohydr. Res. 2004, 339, 2859-2870.
http://dx.doi.org/10.1016/j.carres.2004.10.008
PMid:15582612

[18]. Arsequell, G.; Valencia, G. Tetrahedron: Asymm. 1999, 10, 3045-3094.
http://dx.doi.org/10.1016/S0957-4166(99)00338-9

[19]. Dwek, R. A. Chem. Rev. 1996, 96, 683-720.
http://dx.doi.org/10.1021/cr940283b
PMid:11848770

[20]. Reuter, G.; Gabius, H. J. Cell Mol. Life Sci. 1999, 55, 368-422.
http://dx.doi.org/10.1007/s000180050298
PMid:10228555

[21]. Velter, I.; La Ferla, B.; Nicotra, F. J. Carbohydr. Chem. 2006, 25, 97-138.
http://dx.doi.org/10.1080/07328300600733020

[22]. Dedola, S.; Hughes, D. L.; Nepogodiev, S. A.; Rejzek, M.; Field, R. A. Carbohydrate Res. 2010, 345, 1123-1134.
http://dx.doi.org/10.1016/j.carres.2010.03.041
PMid:20427038

[23]. Anjos, J. V.; Neves Filho, R. A. W.; Nascimento, S- C.; Srivastava, R. M.; Melo, S. J.; Sinou, D. Eur. J. Med. Chem. 2009, 44, 3571-3576.
http://dx.doi.org/10.1016/j.ejmech.2009.03.002
PMid:19345445

[24]. Banday, A. H.; Arora, B. S.; Alam, M. S.; Kumar, H. M. S. Helv. Chim. Acta 2007, 90, 2368-2374.
http://dx.doi.org/10.1002/hlca.200790242

[25]. Zhang, F.; Bernet, B.; Bonnet, V.; Dangles, O.; Sarabia, F.; Vasella, A. Helv. Chim. Acta 2008, 91, 608-617.
http://dx.doi.org/10.1002/hlca.200890064

[26]. Silva, M.; Goncalves, J. C. O.; Oliveira-Campos, A. M. F.; Rodrigues, L. M.; Esteves, A. P. Synth. Commun. 2013, doi: 10.1080/00397911.2011.637655.

[27]. Bock, V. D.; Hiemstra, H.; van Maarseveen, J. A. Eur. J. Org. Chem. 2006, 51-68.
http://dx.doi.org/10.1002/ejoc.200500483

[28]. El Moncef, A.; El Hadrami, El M.; Ben-Tama, A.; Ramirez de Arellano, C.; Zaballos-Garcia, E.; Stiriba, S. -E. J. Mol. Struct. 2009, 929, 6-9.
http://dx.doi.org/10.1016/j.molstruc.2009.03.036

[29]. Kumar, R.; Maulik, P. R.; Misra, A. K. Glycoconjug. J. 2008, 25, 595-602.
http://dx.doi.org/10.1007/s10719-007-9093-5
PMid:18085436

[30]. Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chem. Int. Ed. 2002, 41, 2596-2599.
http://dx.doi.org/10.1002/1521-3773(20020715)41:14<2596::AID-ANIE2596>3.0.CO;2-4

[31]. Pinto, T. A. D.; Hrdina, R.; Kirsch, G.; Oliveira- Campos, A. M. F.; Rodrigues, L. M.; Esteves, A. P. Arkivoc 2012, 6, 185-193.

[32]. Umminger, R.; Friebe, W. G.; Kampe, W.; Roesch, A.; Wilhelms, O. H. US Pat. 4,621,098, 1986.

Supporting Agencies

Foundation for the Science and Technology (FCT, Portugal), FEDER (European Fund for Regional Development)-COMPETE-QREN-EU, VZ MSMT-0021627501, Czech Republic
Most read articles by the same author(s)
TrendMD

Dimensions - Altmetric - scite_ - PlumX
publications
0
supporting
0
mentioning
0
contrasting
0
Smart Citations
0
0
0
0
Citing PublicationsSupportingMentioningContrasting
View Citations

See how this article has been cited at scite.ai

scite shows how a scientific paper has been cited by providing the context of the citation, a classification describing whether it supports, mentions, or contrasts the cited claim, and a label indicating in which section the citation was made.

Downloads and views

Downloads

Metrics

PDF views
835
Jul 2013Jan 2014Jul 2014Jan 2015Jul 2015Jan 2016Jul 2016Jan 2017Jul 2017Jan 2018Jul 2018Jan 2019Jul 2019Jan 2020Jul 2020Jan 2021Jul 2021Jan 2022Jul 2022Jan 2023Jul 2023Jan 2024Jul 2024Jan 2025Jul 2025Jan 202622
|
License Terms

License Terms

by-nc

Copyright © 2025 by Authors. This work is published and licensed by Atlanta Publishing House LLC, Atlanta, GA, USA. The full terms of this license are available at https://www.eurjchem.com/index.php/eurjchem/terms and incorporate the Creative Commons Attribution-Non Commercial (CC BY NC) (International, v4.0) License (http://creativecommons.org/licenses/by-nc/4.0). By accessing the work, you hereby accept the Terms. This is an open access article distributed under the terms and conditions of the CC BY NC License, which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited without any further permission from Atlanta Publishing House LLC (European Journal of Chemistry). No use, distribution, or reproduction is permitted which does not comply with these terms. Permissions for commercial use of this work beyond the scope of the License (https://www.eurjchem.com/index.php/eurjchem/terms) are administered by Atlanta Publishing House LLC (European Journal of Chemistry).