75414-45-8Relevant academic research and scientific papers
Studies on the reaction of D-glucal and its derivatives with 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]Octane salts
Ortner,Albert,Weber,Dax
, p. 297 - 316 (1999)
The reaction of D-glucal and its derivatives with the electrophilic N-F-fluorination reagents F-TEDA tetrafluoroborate and triflate was studied by means of 19F NMR spectroscopy. In all cases mixtures of 2-deoxy-2-fluoro-D-gluco- and -D-mannopyranose derivatives were formed, the ratio of which was dependent on the nature of the O-protecting groups. Concerning the products arising from the direct addition of reagents across the double bond, the D-gluco-configured compounds (13-20) generally showed higher hydrolysis rates than their D-manno-counterparts (21-28). Product separation was only achieved when single anomers (e.g., 2,4-dinitrophenyl glycosides 29e/37e and disaccharidic fluorides 35d/43d) or per-O-acetates (e.g. 29f/37f) were formed.
SYNTHESIS OF 2-DEOXY-2-FLUOROHEXOSES BY FLUORINATION OF GLYCALS IN AQUEOUS MEDIA
Diksic, Mirko,Jolly, Dean
, p. 17 - 24 (2007/10/02)
1,5-Anhydro-2-deoxy-D-arabino- (D-glucal), 1,5-anhydro-2-deoxy-D-lyxo- (D-galactal), and 3,4,6-tri-O-acetyl-1,5-anhydro-2-deoxy-D-lyxo-hex-1-enitol (3,4,6-tri-O-acetyl-D-galactal) (3) were fluorinated in water and organic solvent-water with molecular fluorine and, for 18F-labelled compounds, with 18F>fluorine.Chemical yields of 40 and 10percent were obtained for 2-deoxy-2-fluoro-D-glucose and 2-deoxy-2-fluoro-D-mannose, respectively, and 35 and 5percent for 2-deoxy-2-fluoro-D-galactose (12) and 2-deoxy-2-fluoro-D-talose (13), respectively.In the fluorination of 3, the chemical yields of 12 and 13 were 38 and 6percent, respectively.An l.c. separationof 2-deoxy-2-fluoro-D-hexoses is described.
