Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
Synthesis of Pyrrole Nucleosides by the Photo-dehydrogenation of Δ3-Pyrroline Derivatives
Masajiro KawanaSakae Emoto
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1969 Volume 42 Issue 12 Pages 3539-3546

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Abstract

1-(β-D-Glucopyranosyl)pyrrole (VI) was prepared by the photo-dehydrogenation of 1-(2′,3′,4′,6′-tetra-O-acetyl-β-D-glucopyranosyl)-Δ3-pyrroline (IV) in the presence of oxygen and benzophenone, followed by deacetylation. The nucleoside (VI) was also derived directly from 1-(D-glucosyl)-Δ3-pyrroline (III) by photochemical means. The synthesis of 1-(α-D-ribofuranosyl)-pyrrole (XI), its β-anomer (XII), and 1-(β-D-ribopyranosyl)pyrrole (XIII) was accomplished by photodehydrogenation of 1-(2′,3′-O-isopropylidene-D-ribosyl)-Δ3-pyrroline, followed by the removal of the protecting group. The treatment of 1-(2′,3′-O-isopropylidene-α-D-ribofuranosyl)pyrrole (VIII) with 80% aqueous acetic acid afforded a novel α-cyclonucleoside, 1-(2-C,2′-O-isopropylidene-α-D-ribofuranosyl)pyrrole (XIV), besides XI–XIII. The formation of pyrrole by the photodehydrogenation of Δ3-pyrroline (II) itself was confirmed by gas chromatography.

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