Dye-sensitized photooxygenation of sugar furans: novel bis-epoxide and spirocyclic C-nucleosides

Dye-sensitized photooxygenation of sugar furans: novel bis-epoxide and spirocyclic C-nucleosides

Dye-sensitized photooxygenation of 2-methyl 5-(2,3,5-tri- O-acetyl-β- d-ribofuranosyl)furoate leads to (1 S,4 R)- endo-peroxide, highlighting a high facial diastereoselectivity. This endo-peroxide rearranges into syn-(1 R,2 R:3 S,4 R)-diepoxide C-nucleoside, while by Et 2S-reduction followed by NEt...

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Veröffentlicht in:Tetrahedron 2008-07, Vol.64 (28), p.6744-6748
Hauptverfasser: Astarita, Anna, Cermola, Flavio, Rosaria Iesce, M., Previtera, Lucio
Format: Artikel
Sprache:eng
Schlagworte:
C-nucleosides
Glycosyl furans
Photooxygenation
Singlet oxygen
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Zusammenfassung:Dye-sensitized photooxygenation of 2-methyl 5-(2,3,5-tri- O-acetyl-β- d-ribofuranosyl)furoate leads to (1 S,4 R)- endo-peroxide, highlighting a high facial diastereoselectivity. This endo-peroxide rearranges into syn-(1 R,2 R:3 S,4 R)-diepoxide C-nucleoside, while by Et 2S-reduction followed by NEt 3 catalysis affords a spirocyclic C-nucleoside. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2008.05.002