Studies on the reaction of D-glucal and its derivatives with 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]Octane salts

Article abstract of DOI:10.1080/07328309908543997

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.

Full text of DOI:10.1080/07328309908543997

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Journal of Carbohydrate Chemistry
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Studies on the Reaction of D-
Glucal and its Derivatives with
1-Chloromethyl-4-Fluoro-1,4-
Diazoniabicyclo[2.2.2]Octane Salts
J. Ortner , M. Albert , H. Weber & K. Dax
a Institute of Organic Chemistry, Technical University Graz,
Stremayrgasse 16, A-8010 Graz, Austria
Version of record first published: 27 Feb 2008.
To cite this article: J. Ortner , M. Albert , H. Weber & K. Dax (1999): Studies on the Reaction
of D-Glucal and its Derivatives with 1-Chloromethyl-4-Fluoro-1,4-Diazoniabicyclo[2.2.2]Octane
Salts, Journal of Carbohydrate Chemistry, 18:3, 297-316
To link to this article: http://dx.doi.org/10.1080/07328309908543997
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