Fructopyranose 4-deoxy-4-fluoro

Several fluoro analogs of ketoses have been reported 1,6-dideoxy-1,6-difluoro-D-fructose was readily obtained from 2,3-O-isopropyli-dene-l,6-di-0-p-tolylsulfonyl-)3-D-fructofuranose by treatment with potassium fluoride in 1,2-ethanediol under a stream of carbon dioxide.96 Surprisingly, although the 6-sulfonyloxy group would be expected to be more reactive than the 1-sulfonyloxy group,97-99 no selectivity was observed. The failure to obtain 1-deoxy-l-fluoro-D-fructopyranose96 from 2,3 4,5-di-0-isopropylidene-l-0-(methylsulfonyl) (or p-nitro-phenylsulfonyl)-/3-D-fructopyranose or phenyl 3,4,5-tri-O-acetyl-l-O-(methylsulfonyl)-/3-D-fructopyranoside by treatment with potassium or sodium fluoride in 1,2-ethanediol, N,N-dimethylformamide, or form-amide at elevated temperatures may be attributed to the fact that nu-... 

Deoxy-fructopyranose 1,2-0-Isopropylidene- 4-Fluoro- ElOb,. 145 (Oxirane + KHF2) 6-Deoxy-D-galaclopyranose 1,3 4.5-Di-O-isopropylidene-6-fluoro-... 

Fluorine- and Nitrogen-containing Compounds.- 4-Deoxy- l-fluoro-B-D-fructopyranose, 2,3-dl-O-acetyl-l, 6-anhydro-i<-0-( 3, i, 6-tri-... 

O -Benzoyl-1,2-0 -isopropylidene- p-D-fructopyranose, 1-62 1-0-Benzyl-3-deoxy-3-fluoro-D-fructose, D-74 l-Bromo-l-deoxy-2,3 4,5-di-0-isopropylidene-p-D-fructopyranose, B-67 Butyl p-D-fructofuranoside, F-84... 

Acetylated and Benzoylated Derivatives of Sugars.—1,2,3,5-Tetra-O-acetyl-jS-D-ribofuranose, 3-0-acetyl-jS-L-arabinofuranose 1,2,5-orthobenzoate, (Z)-l-O-acetyl-2,3 4,5-di-0-isopropylidene-D-e/ y/Aw- and -D-/Areo-pent-l-enitol, 2,3,4-tri-O-benzoyl-jS-D-xylopyranosyl chloride, 2,3,4-tri-0-acetyl-j9-D-xyIopyranosyI azide, 1,3,4-tri-0-acetyl-2-deoxy-2-fluoro-a-D-xylopyranose, 1,2,3,4-tetra-O-acetyl-a-D-Iyxopyranose, 2,3,4,6-tetra-0-acetyl-a -D-glucopyranosyl bromide, 3,4,6-tri-0-acetyl-l,2-0-(l-cyanoethyIidene)-a-D-glucopyranose, 3,4,6-tri-O-acetyl-)S-D-mannopyranose l,2-(methyi orthoacetate), 2,3-di-0-acetyI-l,6-anhydro-jS-D-galactopyranose, 2,3,4,6-tetra-0-acetyl-j8-D-galactopyranosyl cyanide, 1,2,3,4,6-penta-O-acetyl-a-D-idopyranose, 1,4,5-tri-0-acetyl-2,3-0-isopropyIidene-)S-D-fructopyranose, and 2,3,4-tri-O-acetyl-a-L-rhamnopyrano-syl and 2,3,4,6-tetra-O-acetyl-a-D-mannopyranosyl chlorides. ... 

---