dc.contributor.author | Esmurziev, Aslan M. | nb_NO |
dc.contributor.author | Simic, Nebojsa | nb_NO |
dc.contributor.author | Hoff, Bard Helge | nb_NO |
dc.contributor.author | Sundby, Eirik | nb_NO |
dc.date.accessioned | 2014-12-19T13:21:06Z | |
dc.date.available | 2014-12-19T13:21:06Z | |
dc.date.created | 2011-04-01 | nb_NO |
dc.date.issued | 2010 | nb_NO |
dc.identifier | 407864 | nb_NO |
dc.identifier.issn | 0732-8303 | nb_NO |
dc.identifier.uri | http://hdl.handle.net/11250/247609 | |
dc.description.abstract | Benzoylated deoxyfluoropyranosides have been synthesized, starting with protected, unprotected, or fluorinated precursors. Fluorination of eight derivatives was compared using DAST and Deoxo-Fluor as reagents. Deoxo-Fluor was found to be especially useful in the fluorination of methyl 2,3,4-O-tribenzoyl -D-mannopyranoside and -D-glucopyranoside, resulting in better yields and avoiding the 1,6-methoxy migration experienced with DAST for one derivative. The two reagents gave comparable yields in the fluorination of other methyl pyranosides, confirming Deoxo-Fluor as a safer alternative to DAST. Methyl -D-mannopyranoside underwent fluorination to yield the 4,6-difluorotalopyranoside and the corresponding cyclic sulfite. The NMR spectroscopic properties of 11 benzoyl deoxy-fluoropyranosides are reported. | nb_NO |
dc.language | eng | nb_NO |
dc.publisher | Norges teknisk-naturvitenskapelige universitet, Fakultet for naturvitenskap og teknologi, Institutt for kjemi | nb_NO |
dc.subject | Deoxyfluorosugars | en_GB |
dc.subject | Diethylaminosulfur trifluoride | en_GB |
dc.subject | Bis-(2-methoxyethyl) aminosulfur trifluoride | en_GB |
dc.subject | DAST | en_GB |
dc.subject | Deoxo-Fluor | en_GB |
dc.subject | Benzoyl pyranosides | en_GB |
dc.subject | 19F NMR | en_GB |
dc.title | Synthesis and Structure Elucidation of Benzoylated Deoxyfluoropyranosides | nb_NO |
dc.type | Journal article | nb_NO |
dc.type | Peer reviewed | nb_NO |
dc.source.pagenumber | 348-367 | nb_NO |
dc.source.volume | 29 | nb_NO |
dc.source.journal | Journal of carbohydrate chemistry | nb_NO |
dc.source.issue | 7 | nb_NO |
dc.identifier.doi | 10.1080/07328303.2010.540055 | nb_NO |
dc.contributor.department | Norges teknisk-naturvitenskapelige universitet, Fakultet for naturvitenskap og teknologi, Institutt for kjemi | nb_NO |