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
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Sprache:eng
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C-nucleosides
Glycosyl furans
Photooxygenation
Singlet oxygen
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container_end_page 6748
container_issue 28
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container_title Tetrahedron
container_volume 64
creator Astarita, Anna
Cermola, Flavio
Rosaria Iesce, M.
Previtera, Lucio
description 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]
doi_str_mv 10.1016/j.tet.2008.05.002
format Article
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source Elsevier ScienceDirect Journals
subjects C-nucleosides
Glycosyl furans
Photooxygenation
Singlet oxygen
title Dye-sensitized photooxygenation of sugar furans: novel bis-epoxide and spirocyclic C-nucleosides
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