Summary
The key step in the preparation of 6-deoxy-1,2-O-isopropylidene-β-L-talofuranose (7) and 6-deoxy-1,2-O-isopropylidene-β-L-idofuranose (13) is the selective exchange of the 6-O-mesyl rest of 3-O-acetyl-5,6-O-dimesyl-1,2-O-isopropylidene-α-D-allofuranose (4) and 3-O-acetyl-5,6-O-dimesyl-1,2-O-isopropylidene-α-D-glucofuranose (10) by acetate group (potassium acetate/18-crown-6).
Zusammenfassung
Schlüsselschritt bei der Herstellung von 6-Desoxy-1,2-O-isopropyliden-β-L-talofuranose (7) und 6-Desoxy-1,2-O-isopropyliden-β-L-idofuranose (13) ist der selektive Austausch der primären Mesyl-Gruppe in 3-O-Acetyl-5,6-O-dimesyl-1,2-O-isopropyliden-α-D-allofuranose (4) und 3-O-Acetyl-5,6-O-dimesyl-1,2-O-isopropyliden-α-D-glucofuranose (10) durch den Acetat-Rest in Gegenwart von Kaliumacetat/Kronen-Ether.
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Hiebl, J., Zbiral, E. Improved synthesis of 6-deoxy-1,2-O-isopropylidene-β-L-talofuranose and 6-deoxy-1,2-O-isopropylidene-β-L-idofuranose. Monatsh Chem 121, 691–695 (1990). https://doi.org/10.1007/BF00809774
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DOI: https://doi.org/10.1007/BF00809774