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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
diethylaminosulfur trifluoride
Fecha de publicación : 2001
Editor: Elsevier
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.
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Citación : Tetrahedron 57(31) : 6733-6743 (2001)
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