The crystal structure of 4,6-Di- O -benzyl-2,3-dideoxy-2,2,3,3- tetrafluorogalactose

Journal of Carbohydrate Chemistry

Volumn 30, Issue 7-9, 2011, Pages 618-625

  Linclau, Bruno ^a   Golten, Samuel ^a   Light, Mark ^a  

^a UNIVERSITY OF SOUTHAMPTON   (United Kingdom)

Author keywords

Fluorinated carbohydrate; Structure; X ray crystal structure

Indexed keywords

EID: 84856321785     PISSN: 07328303     EISSN: 15322327     Source Type: Journal    
DOI: 10.1080/07328303.2011.618895     Document Type: Article

References (28)

1. Sears, P.; Wong, C.-H. Carbohydrate mimetics: A new strategy for tackling the problem of carbohydrate-mediated biological recognition. Angew. Chem. Int. Ed. 1999, 38(16), 2300-2324. (Pubitemid 29399553)
2. Compain, P.; Martin, O.R. Carbohydrate mimetics-based glycosyltransferase inhibitors. Bioorg. Med. Chem. 2001, 9(12), 3077-3092. (Pubitemid 33065608)
3. Gruner, S.A.W.; Locardi, E.; Lohof, E.; Kessler, H. Carbohydrate-based mimetics in drug design: Sugar amino acids and carbohydrate scaffolds. Chem. Rev. 2002, 102(2), 491-514. (Pubitemid 35381637)
4. Koester, D.C.; Holkenbrink, A.; Werz, D.B. Recent advances in the synthesis of carbohydrate mimetics. Synthesis 2010, 3217-3242.
5. Agostino, M.; Sandrin, M.S.; Thompson, P.E.; Farrugia, W.; Ramsland, P.A.; Yuriev, E. Carbohydrate-mimetic peptides: Structural aspects of mimicry and therapeutic implications. Expert Opin. Biol. Ther. 2011, 11(2), 211-224.
6. Kim, H.W.; Rossi, P.; Shoemaker, R.K.; DiMagno, S.G. Structure and transport properties of a novel, heavily fluorinated carbohydrate analogue. J. Am. Chem. Soc. 1998, 120(35), 9082-9083. (Pubitemid 28449195)
7. Biffinger, J.C.; Kim, H.W.; DiMagno, S.G. The polar hydrophobicity of fluorinated compounds. ChemBioChem 2004, 5(5), 622-627. (Pubitemid 39257083)
8. Muller, K.; Faeh, C.; Diederich, F. Fluorine in pharmaceuticals: looking beyond intuition. Science 2007, 317(5846), 1881-1886. (Pubitemid 47509426)
9. Z̈ urcher, M.; Diederich, F.O. Structure-based drug design: Exploring the proper filling of apolar pockets at enzyme active sites. J. Org. Chem. 2008, 73(12), 4345-4361. (Pubitemid 351842449)
10. Boydell, A.J.; Vinader, V.; Linclau, B. Enantioselective synthesis of tetrafluoroethylene-containing monosaccharides. Angew. Chem. Int. Ed. 2004, 43(42), 5677-5679. (Pubitemid 39486648)
11. Bresciani, S.; Lebl, T.; Slawin, A.M.Z.; O'Hagan, D. Fluorosugars: Synthesis of the 2,3,4-trideoxy-2,3,4-trifluoro hexose analogues of d-glucose and d-altrose and assessment of their erythrocyte transmembrane transport. Chem. Commun. 2010, 46(30), 5434-5436.
12. Linclau, B.; Boydell, A.J.; Timofte, R.S.; Brown, K.J.; Vinader, V.; Weymouth- Wilson, A.C. Enantioselective synthesis of tetrafluorinated ribose and fructose. Org. Biomol. Chem. 2009, 7(4), 803-814.
13. Timofte, R.S.; Linclau, B. Enantioselective synthesis of tetrafluorinated glucose and galactose. Org. Lett. 2008, 10(17), 3673-3676.
14. Rao, V.S.R. Conformation of carbohydrates. Harwood Academic Publishers: 1998.
15. Wormald, M.R.; Petrescu, A.J.; Pao, Y.-L.; Glithero, A.; Elliott, T.; Dwek, R.A. Conformational studies of oligosaccharides and glycopeptides: Complementarity of NMR, X-ray crystallography, and molecular modelling. Chem. Rev. 2002, 102(2), 371-386. (Pubitemid 35377620)
16. Gabius, H.-J.; Siebert, H.-C.; Andŕe, S.; Jiḿenez-Barbero, J.; R̈udiger, H. Chemical biology of the sugar code. ChemBioChem 2004, 5(6), 740-764. (Pubitemid 39257059)
17. Amorim, L.; Marcelo, F.; Rousseau, C.; Nieto, L.; Jiḿenez-Barbero, J.; Marrot, J.;Rauter, A.P.; Sollogoub, M.; Bols, M.; Bĺeriot, Y. Direct experimental evidence for the high chemical reactivity of a- and β-xylopyranosides adopting a 2,5B conformation in glycosyl transfer. Chem. Eur. J. 2011, 17(26), 7345-7356, and references cited therein.
18. Linclau, B.; Golten, S.; Light, M.; Sebban, M.; Oulyadi, H. The conformation of tetrafluorinated methyl galactoside anomers: Crystallographic and NMR studies. Carbohydr. Res. 2011, 346(9), 1129-1139.
19. For the synthesis of 5, see ref 13.
20. Cremer, D.; Pople, J.A. General definition of ring puckering coordinates. J. Am. Chem. Soc. 1975, 97(6), 1354-1358.
21. Boeyens, J.C.A. The conformation of six-membered rings. J. Chem. Crystallogr. 1978, 8(6), 317-320.
22. Jeffrey, G.A.; Yates, J.H. Stereographic representation of the Cremer-Pople ringpuckering parameters for pyranoid rings. Carbohydr. Res. 1979, 74(1), 319-322
23. K̈oll, P.; Saak, W.; Pohl, S.; Steiner, B.; Kóos, M. Preparation and crystal and molecular structure of 6-O-[(2S)-2,3-epoxypropyl]-1, 2:3,4-di-O-isopropylidene-[alpha]- d-galactopyranose. Pyranoid ring conformation in 1,2:3,4-di-O-isopropylidene galactopyranose and related systems. Carbohydr. Res. 1994, 265(2), 237-248. (Pubitemid 24377130)
24. Dunitz, J.D.; Schweizer, W.B. Molecular pair analysis: C-HF interactions in the crystal structure of fluorobenzene? And related matters. Chem. Eur. J. 2006, 12(26), 6804-6815. (Pubitemid 44369214)
25. Reichenbacher, K.; Suss, H.I.; Hulliger, J. Fluorine in crystal engineering-the little atom that could. Chem. Soc. Rev. 2005, 34(1), 22-30. (Pubitemid 40311180)
26. Thalladi, V.R.; Weiss, H.-C.; Bl̈aser, D.; Boese, R.; Nangia, A.; Desiraju, G.R. C-HF interactions in the crystal structures of some fluorobenzenes. J. Am. Chem. Soc. 1998, 120(34), 8702-8710. (Pubitemid 28442908)
27. Mehta, G.; Sen, S. Probing fluorine interactions in a polyhydroxylated environment: Conservation of a C-F-H-C recognition motif in presence of O-H-O hydrogen bonds. Eur. J. Org. Chem. 2010, 2010(18), 3387-3394.
28. Withers, S.G.; Street, I.P.; Rettig, S.J. The preferred conformation of 2-fluoro-2- deoxy β-D-mannopyranosyl fluoride. An X-ray crystallographic and 2-dimensional proton nuclear magnetic resonance study. Can. J. Chem. 1986, 64(2), 232-236.