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The hydroformylation of 3,4-Di-O-acetyl-D-xylal

University of British Columbia

3,4-Di-0-acetyl-D-xylal was treated in the presence of dicobalt octacarbonyl with carbon monoxide and hydrogen at elevated temperatures and pressures. From deacetylation of the reaction products, 1-∝(or β)-hydroxymethyl-2-hydro-D-xylal and l-∝(or β)-formyl-2-hydro-D-xylal were obtained; that is, a hydroxymethyl group and a formyl group were added respectively at carbon one of the original unsaturated sugar. Sodium borohydride reduction in aqueous solution of 1-∝(or β)-formyl-2-hydro-D-xylal produced 1-∝ (or β)-hydroxy-methyl-2-hydro-D-xylal. 1-∝(or β)-Formyl-2-hydro-D-xylal gave an acetate which is described. Periodate oxidation of the sugar alcohol gave the dialdehyde which on treatment with p-nitrophenylhydrazine hydrochloride yielded glyoxal-bis-p-nitrophenylhydrazone and 2-deoxy-D, L-tetrose p-nitrophenylhydrazone as major degradation products.

Text

2011-12-01

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http://hdl.handle.net/2429/39425

Chemistry

University of British Columbia

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