5-Deoxy-5-Fluoro-D-Glucofuranose and -L-Idofuranose Synthesis and NMR Studies
Titel:
5-Deoxy-5-Fluoro-D-Glucofuranose and -L-Idofuranose Synthesis and NMR Studies
Auteur:
Albert, R. Dax, K. Seidl, S. Sterk, H. Stutz, A. E.
Verschenen in:
Journal of carbohydrate chemistry
Paginering:
Jaargang 4 (1985) nr. 4 pagina's 513-520
Jaar:
1985-12-01
Inhoud:
Starting from 1,2-O-isopropylidene-α-D-gluco- and -β-L-ido-furanurono-6,3-lactone, 5-deoxy-5-fluoro-α/β-D-gluco- and -L-idofuranose, respectively, were prepared by the following sequence of reactions: trifluoromethanesulfonylation, nucleophilic substitution with inversion of configuration, lactone reduction and deprotection. On the basis of H-H-, H-C-, H-F-, and C-F-couplings, the stereochemistry of the products is discussed.