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

Authors
Aghmiz, ML Diaz, Y Jana, GH Matheu, MI Echarri, R Castillon, S Jimeno, ML
Citation
Ml. Aghmiz et al., The reaction of pyranoside 2-uloses with DAST revised. Synthesis of 1-fluoro-ketofuranosyl fluorides and their reactivity with alcohols, TETRAHEDRON, 57(31), 2001, pp. 6733-6743
Citations number
25
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
57
Issue
31
Year of publication
2001
Pages
6733 - 6743
Database
ISI
SICI code
0040-4020(20010730)57:31<6733:TROP2W>2.0.ZU;2-A
Abstract
We have reinvestigated the reaction of alpha -pyranosides-2-uloses 13, 14, 19 and 24 with DAST and shown that the 1,2-difluorinated compounds 17, 18 a nd 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 spira nic compounds 29-31. The reaction of 17 with bis(trimethylsilyl)uracil prod uced the mononucleoside 28, which preserves the fluorine atom in the more s ubstituted carbon. (C) 2001 Elsevier Science Ltd. All rights reserved.