H. Ando, J. Yoshimura
Sep 1, 1970
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0
Influential Citations
4
Citations
Journal
Bulletin of the Chemical Society of Japan
Abstract
3-Acetamido-3,5-dideoxy-1,2-O-isopropylidene-α-D-ribofuranose (5) was synthesized through two pass-ways: 1) starting from 3-acetamido-3-deoxy-1,2-O-isopropylidene-α-D-allofuranose which is obtained from D-glucose, through five steps; periodate oxidation, hydrogenation, 5-O-tosylation, 5-iodination and hydrogenation: 2) starting from l,2-O-isopropylidene-3,5-di-O-tosyl-α-D-xylofuranose through four steps; 5-iodination, hydrogenation, 3-amination and N-acetylation. Total yields in the two pass-ways were 12.7% and 7.6% from the parent aldoses, respectively. Hydrolysis of 5 gave the titled compound as a sirup, which was converted to the crystalline osazone. The structure and conformation of intermediates in these syntheses were examined by NMR spectroscopy.