Synthesis of (6-2H)- and 6-deoxy-6-fluoro-L-galactose derivatives

Journal of Carbohydrate Chemistry

Volumn 20, Issue 1, 2001, Pages 31-43

  Brackhagen, Meinolf ^a   Boye, Hanna ^a   Vogel, Christian ^a  

^a UNIVERSITY OF ROSTOCK   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0035531153     PISSN: 07328303     EISSN: None     Source Type: Journal    
DOI: 10.1081/CAR-100102541     Document Type: Article

References (9)

1. Brackhagen, M.; Vogel, C. Abstract B-389, 20th International Carbohydrate Symposium, Hamburg, Germany, August 27-September 1, 2000; Thiem, J., Eds.; LCI Publisher GmbH: Hamburg, 2000. Part IV of the series "L-Fucose Derivatives", for part III see ref. 2.
2. Vogel, C.; Bergemann, C.; Ott, A.-J.; Lindhorst, T.K.; Thiem, J.; Dahlhoff, W.V.; Hällgren, C.; Palcic, M.M.; Hindsgaul, O. Synthesis of Carbon-Backbone-Elongated GDP-L-Fucose Derivatives as Substrates for Fucosyltransferase-Catalysed Reactions. Liebigs Ann./Recueil 1997, 601-612.
3. Kristen, H.; Vogel, C.; Wrubel, F.; Mahrwald, R.; H. Schick, H. Introduction of a New Selective Oxidation Procedure into Carbohydrate Chemistry. An Efficient Conversion of D-Galactose into L-Fucose. J. Carbohydr. Chem. 1988, 7, 277-281.
4. Vogel, C.; Boye, H.; Kristen, H. Galacturonate aus Acetyl- und Isopropyliden-D-galactopyranosen. J. Prakt. Chem.1990, 332, 28-36, and references therein.
5. Lee, H.H.; Hodgson, P.G.; Bernacki, R.J.; Korytnyk, W.; Sharma, M. Analogs of Cell Surface Carbohydrates. Synthesis of D-Galactose Derivatives Having an Ethynyl, Vinyl or Epoxy Residue at C-5. Carbohydr. Res. 1988, 176, 59-72.
6. May, J.A., Jr.; Sartorelli, A.C. Synthesis and Biological Activity of Potential Antimetabolites of L-Fucose. J. Med. Chem. 1979, 22, 971-976.
7. Barrette, E.-P.; Goodman, L. Convenient and Stereospecific Synthesis of Deoxy Sugars. Reductive Displacement of Trifluoromethanesulfonates. J. Org. Chem. 1984, 49, 176-178.
8. Doboszewski, B.; Hay, G.W.; Szarek, W.A. The Rapid Synthesis of Deoxyfluoro Sugars Using Tris(dimethylamino)sulfonium Difluorotrimethylsilicate (TASF). Can. J. Chem. 1987, 65, 412-419.
9. Perrin, D.D.; Armarego, W.L.F. Purification of Laboratoy Chemicals. 3rd Ed.; Pergamon Press: Oxford, 1988.