Display options
Cite
Šnajdr I, Parkan K, Hessler F, et al. Cross-metathesis reaction of α- and β-vinyl C-glycosides with alkenes. Beilstein J Org Chem. 2015;11:1392-7doi: 10.3762/bjoc.11.150.
Šnajdr, I., Parkan, K., Hessler, F., & Kotora, M. (2015). Cross-metathesis reaction of α- and β-vinyl C-glycosides with alkenes. Beilstein journal of organic chemistry, 111392-7. https://doi.org/10.3762/bjoc.11.150
Šnajdr, Ivan, et al. "Cross-metathesis reaction of α- and β-vinyl C-glycosides with alkenes." Beilstein journal of organic chemistry vol. 11 (2015): 1392-7. doi: https://doi.org/10.3762/bjoc.11.150
Šnajdr I, Parkan K, Hessler F, Kotora M. Cross-metathesis reaction of α- and β-vinyl C-glycosides with alkenes. Beilstein J Org Chem. 2015 Aug 10;11:1392-7. doi: 10.3762/bjoc.11.150. eCollection 2015. PMID: 26425194; PMCID: PMC4578437.
Copy Download .nbib Format: NLM
Share it on

Beilstein J Org Chem. 2015 Aug 10;11:1392-7. doi: 10.3762/bjoc.11.150. eCollection 2015.

Cross-metathesis reaction of α- and β-vinyl C-glycosides with alkenes.

Beilstein journal of organic chemistry

Ivan Šnajdr, Kamil Parkan, Filip Hessler, Martin Kotora

Affiliations

  1. Department of Organic Chemistry, Charles University in Prague, Hlavova 8, 153 00 Praha 2, Czech Republic.
  2. Department of Chemistry of Natural Compounds, University of Chemistry and Technology, Prague, Technická 5, 160 00 Praha 6, Czech Republic.

PMID: 26425194 PMCID: PMC4578437 DOI: 10.3762/bjoc.11.150

Abstract

Cross-metathesis of α- and β-vinyl C-deoxyribosides and α-vinyl C-galactoside with various terminal alkenes under different conditions was studied. The cross-metathesis of the former proceeded with good yields of the corresponding products in ClCH2CH2Cl the latter required the presence of CuI in CH2Cl2 to achieve good yields of the products. A simple method for the preparation of α- and β-vinyl C-deoxyribosides was also developed. In addition, feasibility of deprotection and further transformations were briefly explored.

Keywords: C-glycosides; carbohydrates; catalysis; cross-metathesis; ruthenium

References

  1. Org Biomol Chem. 2011 Sep 7;9(17):5934-7 - PubMed
  2. Org Lett. 2007 Dec 6;9(25):5311-4 - PubMed
  3. Org Lett. 2003 Mar 6;5(5):625-8 - PubMed
  4. Org Lett. 2007 Oct 25;9(22):4443-6 - PubMed
  5. Org Lett. 2004 Oct 28;6(22):4077-80 - PubMed
  6. Methods Enzymol. 2003;362:17-28 - PubMed
  7. Chem Rev. 2010 Mar 10;110(3):1746-87 - PubMed
  8. J Am Chem Soc. 2009 Mar 25;131(11):3923-33 - PubMed
  9. Org Lett. 2005 Jun 9;7(12):2385-8 - PubMed
  10. J Org Chem. 2009 Jan 16;74(2):925-8 - PubMed
  11. Bioorg Med Chem Lett. 2009 Jun 15;19(12):3316-9 - PubMed
  12. J Med Chem. 2010 Oct 14;53(19):6947-53 - PubMed
  13. J Med Chem. 2009 Sep 24;52(18):5753-7 - PubMed
  14. Future Med Chem. 2014 Jun;6(10):1201-29 - PubMed
  15. J Org Chem. 2011 Jun 3;76(11):4697-702 - PubMed
  16. Eur J Med Chem. 2014 Aug 18;83:389-97 - PubMed
  17. J Am Chem Soc. 2003 Sep 17;125(37):11360-70 - PubMed
  18. J Org Chem. 2005 Nov 11;70(23):9636-9 - PubMed
  19. Org Biomol Chem. 2009 Nov 7;7(21):4369-77 - PubMed
  20. Chem Commun (Camb). 2008 Dec 21;(47):6282-4 - PubMed
  21. Chemistry. 2011 Nov 11;17(46):12981-93 - PubMed
  22. Chemistry. 2003 Mar 17;9(6):1296-302 - PubMed
  23. J Am Chem Soc. 2010 Dec 1;132(47):16805-11 - PubMed

Publication Types