T. Hanaya, A. Akamatsu, Heizan Kawamoto
Aug 1, 1991
Citations
0
Influential Citations
10
Citations
Journal
Bulletin of the Chemical Society of Japan
Abstract
(5R and 5S)-3-O-Acetyl-5-deoxy-1,2-O-isopropylidene-5-[(methoxy)phenylphosphinyl]-6-O-(tetrahydro-2-pyranyl)-α-D-xylo-hexofuranoses (7) were prepared from 3-O-acetyl-5,6-dideoxy-6-nitro-α-D-xylo-hex-5-enofuranose in 4 steps. Reduction of 7 with sodium dihydridobis(2-methoxyethoxy)aluminate followed by acid hydrolysis provided the title compounds, among which the 5-deoxy-5-phenylphosphino-D-glucoses are the first example of hexopyranose analogs having a phosphinidene group in place of hemiacetal ring-oxygen. These compounds were converted into 1,2,3,4,6-penta-O-acetates, whose structures were established by spectroscopy.