The reaction of pyranoside 2-uloses with DAST revised. Synthesis of 1-fluoro-ketofuranosyl fluorides and their reactivity with alcohols

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 t...

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Bibliographic Details
Published in:Tetrahedron 2001-07, Vol.57 (31), p.6733-6743
Main Authors: Aghmiz, Mohamed L, Dı́az, Yolanda, Jana, Gour Hari, Matheu, M.Isabel, Echarri, Raouf, Castillón, Sergio, Jimeno, M.Luisa
Format: Article
Language:English
Subjects:
carbohydrates
diethylaminosulfur trifluoride
fluorination
glycosylation
spiroacetals
uloses
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Summary: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. Graphic
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(01)00620-2