Synthesis and Structure Elucidation of Benzoylated Deoxyfluoropyranosides
| العنوان: | Synthesis and Structure Elucidation of Benzoylated Deoxyfluoropyranosides |
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| المؤلفون: | Eirik Sundby, Aslan M. Esmurziev, Bård Helge Hoff, Nebojsa Simic |
| المصدر: | Journal of Carbohydrate Chemistry. 29:348-367 |
| بيانات النشر: | Informa UK Limited, 2010. |
| سنة النشر: | 2010 |
| مصطلحات موضوعية: | Diethylaminosulfur trifluoride, chemistry.chemical_compound, Sulfite, Chemistry, Reagent, Yield (chemistry), Organic Chemistry, Organic chemistry, Fluorine-19 NMR, Biochemistry |
| الوصف: | 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 α-D-mannopyranoside and β-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 α-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. |
| تدمد: | 1532-2327 0732-8303 |
| الوصول الحر: | https://explore.openaire.eu/search/publication?articleId=doi_________::4cea8b466e06fc6e670a005f44972726Test https://doi.org/10.1080/07328303.2010.540055Test |
| رقم الانضمام: | edsair.doi...........4cea8b466e06fc6e670a005f44972726 |
| قاعدة البيانات: | OpenAIRE |
| تدمد: | 15322327 07328303 |
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