ISSN:
1573-8353
Quelle:
Springer Online Journal Archives 1860-2000
Thema:
Chemie und Pharmazie
Notizen:
Abstract The possibilities of the direct glycosylation of indoles with glycosyl halides that do not contain participating groups in the 2 position were studied. The α and β anomers of the corresponding C-ribofuranosides were obtained by the reaction of indole or its 5-bromo and 5- or 6-nitro derivatives with 2,3-O-isopropylidene-5-O-p-nitrobenzoyl-D-ribofuranosyl bromide in refluxing benzene in the presence of silver oxide and molecular sieves. O-Substituted 3-α-D-ribofuranosides of indoles undergo isomerization to the 3-β-anomers. Mixtures of anomeric 3,2′-deoxy-D-ribofuranosyl-6-nitroindoles and 1,2′-deoxy-D-ribofuranosyl-6-nitroindoles were synthesized. The structures of the compounds obtained were confirmed by data from PMR, IR, UV, and circular dichroism spectroscopy and mass spectrometry.
Materialart:
Digitale Medien
URL:
http://dx.doi.org/10.1007/BF00503480
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