Showing papers by "Seiichiro Ogawa published in 1970"

Proton Magnetic Resonance Studies on Specifically Deuterated Sucrose Acetates

Abstract: In the proton magnetic resonance spectrum of octa-O-acetylsucrose, an individual acetoxy group signal was assigned by direct comparisons of the spectra of specifically deuterated octa-O-acetylsucroses and that of nondeuterated one. The structures of 2,3,6,3′,4′-penta-O-acetylsucrose and 2,3,4,3′,4′-penta-O-acetylsucrose were further confirmed definitively by the present studies.

Aminocyclitols. XXII. A Synthesis of Actinamine and Hyosamine

Abstract: Hydrazinolysis of 2,4,5,6-tetra-O-acetyl-1,3-di-O-p-toluenesulfonyl-myo-inositol, followed by catalytic hydrogenation afforded myo-inosadiamine-1,3 via an intermediary 6,7-diazabicyclo[3.2.1]-octane-2,3,4,8-tetrol. In this reaction, the use of N,N′-dimethylhydrazine and N-methylhydrazine, instead of hydrazine, gave actinamine: a component of an antibiotic spectinomycin, and N-methyl-myo-inosadiamine-1,3: an important intermediary compound for a synthesis of DL-hyosamine, respectively. Details of the convenient syntheses of actinamine and DL-hyosamine are described.

Aminocyclitols. XXIV. Synthesis of Inosamines from Bromodeoxyinositols

Abstract: Seven inosamines (scyllo, chiro-1, myo-2, myo-4, allo-5, neo-1 and chiro-3) have been prepared from four bromodeoxyinositols [scyllo, chiro-1, allo-5 and neo-1). When bromodeoxyinositols were treated with sodium azide in boiling aqueous 2-methoxyethanol or dimethylformamide, followed by acetylation, pentaacetyl azidodeoxyinositols were obtained in 60–80% yield. On catalytic hydrogenation using Adams’ platinum oxide, the azido compounds yielded hexaacetyl inosamines in good yields. Proton magnetic resonance (PMR) spectra of acetyl azidodeoxyinositols have been studied.