Collect. Czech. Chem. Commun. 2000, 65, 610-620

Homologation of O-Acetylated Methyl Hexopyranosides with a Grignard C1 Reagent

Barbara Grzeszczyk and Aleksander Zamojski*

Institute of Organic Chemistry, Polish Academy of Sciences, 01-224 Warsaw, Poland


Three methyl 2,3,4-tri-O-acetyl-α-D-hexopyranosides of the manno, gluco, and galacto configuration were oxidized to the corresponding methyl hexodialdo-1,5-pyranosides and then reacted with allyloxymethylmagnesium chloride. Methyl heptopyranosides of the D- and L-glycero-α-D-manno-, -α-D-gluco, and -α-D-galacto configuration were obtained in moderate yields. Migration of the 4-O-acetyl group in the products was observed. An interpretation of the results was proposed.

Keywords: Homologation reactions; Carbohydrates; Heptoses; Heptopyranosides; Grignard reagents; Aldehydes; Additions; Allyloxymethylmagnesium chloride.

References: 17 live references.