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|Título :||The reaction of pyranoside 2-uloses with DAST revised. Synthesis of 1-fluoro-ketofuranosyl fluorides and their reactivity with alcohols|
|Autor :||Aghmiz, Mohamed L., Díaz, Yolanda, Jana, Gour Hari, Matheu, M. Isabel, Echarri, Raouf, Castillón, Sergio, Jimeno, M. Luisa|
|Palabras clave :||carbohydrates|
|Fecha de publicación :||2001|
|Resumen:||We have reinvestigated the reaction of α-pyranosides-2-uloses 13, 14, 19 and 24 with DAST and shown that the 1,2-difluorinated compounds 17, 18 and 25 are produced by a ring-contraction reaction. The reaction of 18 with benzyl alcohol gives the tri-benzyl derivative 26 or compound 27, depending on the reaction conditions. Treating 17 with 2-naphthol produced the spiranic compounds 29–31. The reaction of 17 with bis(trimethylsilyl)uracil produced the mononucleoside 28, which preserves the fluorine atom in the more substituted carbon.|
|Versión del editor:||http://bit.ly/ii162Y|
|Citación :||Tetrahedron 57(31) : 6733-6743 (2001)|
|Appears in Collections:||(CENQUIOR) Artículos|
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