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
Hauptverfasser: Flekhter, Oxana B, Baltina, Lidiya A, Tolstikov, Genrikh A
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).
ISSN:0163-3864
1520-6025
DOI:10.1021/np990273b