Glycals in the Stereoselective Synthesis of Triterpene 2-Deoxy-α-l-Glycosides under Conditions of Acidic Catalysis
3β-Hydroxy triterpenes of the oleanane, ursane, and lupane types were successfully glycosylated with acetylated l-glucal and l-rhamnal under conditions of acidic catalysis (anhydrous cation-exchange resin and LiBr). The 2-deoxy- and 2,6-dideoxy-α-l-arabino-hexopyranosides (1−5) were stereoselectivel...
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Veröffentlicht in: | Journal of natural products (Washington, D.C.) D.C.), 2000-07, Vol.63 (7), p.992-994 |
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Hauptverfasser: | , , |
Format: | Artikel |
Sprache: | eng |
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Zusammenfassung: | 3β-Hydroxy triterpenes of the oleanane, ursane, and lupane types were successfully glycosylated with acetylated l-glucal and l-rhamnal under conditions of acidic catalysis (anhydrous cation-exchange resin and LiBr). The 2-deoxy- and 2,6-dideoxy-α-l-arabino-hexopyranosides (1−5) were stereoselectively prepared in 83−90% yields, following deacetylation under mild conditions, which led to the target triterpene 2-deoxy-α-l-glycosides (6−10). |
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ISSN: | 0163-3864 1520-6025 |
DOI: | 10.1021/np990273b |