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Reactions of saccharides catalyzed by molybdate ions . 35. Preparation of D-erythro-L-glucooctose and D-erythro-L-mannooctose

V. Bílik, J. Alfőldi, and M. Matulová

Institute of Chemistry, Centre for Chemical Research, Slovak Academy of Sciences, CS-842 38 Bratislava

 

Abstract: Sodium salts of the epimeric 1-deoxy-l-nitrooctitols obtained by nitromethane synthesis with D-glycero-D-galactoheptose were converted by hydrogen peroxide under catalytic action of molybdate ions into D- erythro -L-glucooctose and D- erythro -L-mannooctose. Molybdate-catalyzed epimerization of D- erythro -L-mannooctose led to a mixture of epimeric aldooctoses in which D-erythro-L-glucooctose predominated. The aldooctoses occur in pyranoid structures in aqueous solutions and their complexing with molybdate ions induces furanoid structures.

Full paper in Portable Document Format: 406a763.pdf

 

Chemical Papers 40 (6) 763–771 (1986)

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