Fluorinated carbohydrates

Foster, A. B.; Hems, R.; Webber, J. M.

doi:10.1016/s0008-6215(00)80504-2

Cited by 99 publications

(26 citation statements)

References 35 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…There is also a close similarity between the ring-proton couplings of compounds 3 continuation of that assumption into the present discussion would clearly require the conclusion that 3 favors the V, conformation, E. In any event, a chemically significant fact emerges from the inter-comparison between derivatives 3 and 17. Namely, that the inversion of configuration at C-4 causes the furanose ring to change its conformation.…”

Section: -Di-0-isopropylidene-a-d-erythro-hex-3-enofu-mentioning

confidence: 63%

See 1 more Smart Citation

Fluorinated carbohydrates. Part VI. Studies of derivatives of 3-deoxy-3-fluoro-D-galactose

Brimacombe¹,

Foster²,

Hems³

et al. 1970

Can. J. Chem.

Self Cite

View full text Add to dashboard Cite

Section: -Di-0-isopropylidene-a-d-erythro-hex-3-enofu-mentioning

confidence: 63%

“…ranose (7) (2) and 3-deoxy-3-fluoro-l,2:5,6-di-0-isopropylidene-a-D-galactofuranose (3) in the ratio ca. 1 : 1.3.…”

Section: -Di-0-isopropylidene-a-d-erythro-hex-3-enofu-mentioning

confidence: 99%

Fluorinated carbohydrates. Part VI. Studies of derivatives of 3-deoxy-3-fluoro-D-galactose

Brimacombe¹,

Foster²,

Hems³

et al. 1970

Can. J. Chem.

Self Cite

View full text Add to dashboard Cite

“…The selective introduction of fluorine into a furanose ring was demonstrated by the reaction of TASF with 1,2:5,6-di-0-isopropylidene-3 -0 -trifluoromethanesulfonyl -a-D -allofuranose (12b), which gave a 66% yield of 3-deoxy-3-fluoro-l,2:5,6-di-0-isopropylidene-a-D-glucofuranose (25) (54). The isomeric triflate 13b, having the D-gluco configuration, reacted with TASF under the same conditions to give an 83% yield of the elimination product, 3-deoxy-1,2 : 5,6-di-0-isopropylidene-a-D-erythro-hex-3-enofuranose (26) (554, but no fluorine-containing product was detected.…”

mentioning

confidence: 99%

The rapid synthesis of deoxyfluoro sugars using tris(dimethylamino)sulfonium difluorotrimethylsilicate (TASF)

Doboszewski¹,

Hay²,

Szarek³

1987

Can. J. Chem.

View full text Add to dashboard Cite

. 65, 412 (1987). Deoxyfluoro sugars were synthesized rapidly by the reaction of trifluoromethanesulfonyl derivatives of partially protected sugars with tris(dimethylarnino)sulfonium difluorotrimethylsilicate (TASF) under mild conditions. The displacements occurred with inversion of configuration; fluorine has been introduced stereospecifically at each of the secondary alcoholic sites of aldohexopyranosides and in one example of a furanoid system. In some instances unsaturated compounds that contained no fluorine were produced. BOGDAN DOBOSZEWSKI, GEORGE W. HAY et WALTER A. SZAREK. Can. J. Chem. 65,412 (1987). On a realist une synthkse rapide de sucres dtsoxyfluorCs en faisant rCagir des derives trifluoromCthanesulfonylCs de sucres partiellement proteges avec du difluorotrimCthylsilicate de tris(dimCthy1amino)sulfonium (TASF), utilisant des conditions douces. Les reactions de deplacement se font avec inversion de configuration; on a pu introduire d'une facon spkcifique des atomes de fluor au niveau de chacun des sites alcooliques secondaires des aldohexopyrannosides et dans un exemple de systtme furannoide. Dans quelques cas, on a obtenu des compos6s insatures qui ne contenaient pas de fluor.[Traduit par la revue]

show abstract

“…ions (5)(6)(7)(8). In a preliminary study we found that the reaction of 3-0-acetyl-1,2-0-isopropylidene-5,6-di-O-mesyl-a-~-glucof~1ranose (3) with anhydrous potassium fluoride, in anhydrous ethylene glycol, afforded a crystalline product in ca.…”

Section: Discussionmentioning

confidence: 99%

Studies of specifically fluoridated carbohydrates. Part V. Derivatives of 3,6-anhydro-5-deoxy-5-fluoro-1,2-O-isopropylidene-α-L-idofuraeose

Hall¹,

Steiner²

1970

Can. J. Chem.

View full text Add to dashboard Cite

The facile synthesis of 3,6-anhydro-5-deoxy-5-fluoro-1,2-O-isoprcpylidene-cc-~-idofuranose (4) from readily available precursors is described. The 'H and 19F nuclear magnetic resonance spectra of this derivative have been analyzed. Interestingly, the fluorine substituent exhibits detectable spin coupling with all ring protons except H-2. Both of the anomeric 1,2-di-0-acetyl derivatives of (4) IntroductionWe have previously described (2, 3) studies of pyranosyl fluoride derivatives which illustrate the potential which fluorine nuclear magnetic resonance (19F n.m.r.) spectroscopy has as a sensitive "probe" for studying pyranose derivatives. In order to apply the "F n.m.r. technique to the more difficult problems associated with furanose systems, it was felt necessary to have previously studied some derivatives having reasonably defined conformations. The 3,6-anhydro-1,2-0-isopropylidene-hexofuranose system (1, 2) seemed admirably suited for this purpose. Earlier proton magnetic resonance (p.m.r.) studies (4) had shown the conformation of this system to be relatively insensitive to changes in the nature of the ring substituents. Thus, as far as is possible for a furanose derivative, this would appear to be a conformationally "rigid" system.

show abstract

Fluorinated carbohydrates

Cited by 99 publications

References 35 publications

Fluorinated carbohydrates. Part VI. Studies of derivatives of 3-deoxy-3-fluoro-D-galactose

Fluorinated carbohydrates. Part VI. Studies of derivatives of 3-deoxy-3-fluoro-D-galactose

The rapid synthesis of deoxyfluoro sugars using tris(dimethylamino)sulfonium difluorotrimethylsilicate (TASF)

Studies of specifically fluoridated carbohydrates. Part V. Derivatives of 3,6-anhydro-5-deoxy-5-fluoro-1,2-O-isopropylidene-α-L-idofuraeose

Contact Info

Product

Resources

About