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  • Title: Homologation of methyl 2-azido- and 2-acetamido-3,4-di-O-benzyl-2-deoxy-D-hexopyranosides with allyloxymethylmagnesium chloride.
    Author: Grzeszczyk B, Zamojski A.
    Journal: Carbohydr Res; 2001 May 18; 332(2):225-34. PubMed ID: 11434382.
    Abstract:
    Methyl 2-azido-2-deoxy-hexodialdo-1,5-pyranosides of the alpha-, beta-D-gluco and alpha-D-manno configuration as well as methyl 2-acetamido-2-deoxy-hexodialdo-1,5-pyranosides of the alpha- and beta-D-gluco configuration, protected at positions 3 and 4 with O-benzyl groups were reacted with an excess of allyloxymethylmagnesium or (phenyldimethylsilyl)methylmagnesium chlorides to afford mixtures of C-6 stereoisomeric heptopyranosides. Configuration of the products separated by column chromatography was assigned by 1H NMR data.
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