Unprotected carbohydrates as starting material in chemical synthesis: Not just a challenge but an opportunity

Synlett

Volumn 26, Issue 4, 2015, Pages 421-425

  Saloranta, Tiina ^a   Leino, Reko ^a  

^a ÅBO AKADEMI UNIVERSITY   (Finland)

Author keywords

carbohydrates; chemoselectivity; chiral pool; green chemistry; regioselectivity

Indexed keywords

ALDEHYDE; CARBOHYDRATE; MONOSACCHARIDE;

ALLYLATION; ARTICLE; CATALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; DERIVATIZATION; GLYCOSYLATION; OXIDATION; SYNTHESIS;

EID: 84925494056     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0034-1379979     Document Type: Article

References (21)

1. For a review on protecting-group-free synthesis, see: Young I. S., Baran P. S. Nat. Chem.: 2009; 1 193
2. Carbohydrates. Osborn H. M. I. Elsevier Science Oxford: 2003
3. For a review, see: Hsu C.-H, Hung S.-C, Wu C.-Y, Wong C.-H. Angew. Chem. Int. Ed.: 2011; 50 11872
4. For the exact compositions of the tautomeric mixtures for aldohexoses determined by studying the equilibrium of 13C-labeled compounds by 13C NMR spectroscopy, see: Zhu Y., Zajicek J., Serianni A. S. J. Org. Chem.: 2001; 66 6244
5. For a comprehensive review on methods for shortening and lengthening the carbon chain in carbohydrates, see: Monrad R. N., Madsen R. Tetrahedron: 2011; 67 8825
6. Kiliani H. Ber. Dtsch. Chem. Ges.: 1886; 19 767
7. Fischer E. J. Am. Chem. Soc.: 1890; 12 461
8. Lundt I., Madsen R. Synthesis: 1995; 787
9. Hotchkiss D., Soengas R., Simone M. I., van Ameijde J., Hunter S., Cowley A. R., Fleet G. W. J. Tetrahedron Lett.: 2004; 45 9461
10. Soengas R., Izumori K., Simone M. I., Watkin D. J., Skytte U. P., Soetaert W., Fleet G. W. J. Tetrahedron Lett.: 2005; 46 5755
11. Railton C. J., Clive D. L. J. Carbohydr. Res.: 1996; 218 69
12. Jorgensen M., Iversen E. H., Madsen R. J. Org. Chem.: 2001; 66 4625
13. Voigt B., Scheffler U., Mahrwald R. Chem. Commun.: 2012; 48 5304
14. Voigt B., Matviitsuk A., Mahrwald R. Tetrahedron: 2013; 69 4302
15. Pfaffe M., Mahrwald R. Org. Lett.: 2012; 14 792
16. Schmalisch S., Mahrwald R. Org. Lett.: 2013; 15 5854
17. Matviitsuk A., Berndt F., Mahrwald R. Org. Lett.: 2014; 16 5474
18. Farnandez-Megia E., Correa J., Rodríguez-Meizoso I., Riguera R. Macromolecules: 2006; 39 2113
19. Ladmiral V., Mantovani G., Clarkson G. J., Cauet S., Irwin J. L., Haddleton D. M. J. Am. Chem. Soc.: 2006; 128 4823
20. Gouin S. G., Kovensky J. Tetrahedron Lett.: 2007; 48 2875
21. Besset C., Chambert S., Fenet B., Queneau Y. Tetrahedron Lett.: 2009; 50 7043