Homologation of methyl 2-azido- and 2-acetamido-3,4-di-O-benzyl-2-deoxy-D-hexopyranosides with allyloxymethylmagnesium chloride.
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.
Grzeszczyk
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Institute of Organic Chemistry, Polish Academy of Sciences, Warsaw.
Zamojski
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D002236:Carbohydrate Conformation; D002942:Circular Dichroism; D003837:Deoxy Sugars / Q000737:chemistry; D008759:Methylglycosides / Q000138:chemical synthesis*; D019906:Nuclear Magnetic Resonance, Biomolecular; D009942:Organometallic Compounds / Q000737:chemistry*
C440779:(phenyldimethylsilyl)magnesium chloride; D003837:Deoxy Sugars; D008759:Methylglycosides; D009942:Organometallic Compounds; C440778:allyloxymethylmagnesium chloride