Synthesis of 5-Deoxy-5-phenylphosphino- and 5-Phenylphosphinyl-D-glucopyranoses.
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概要
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(5<I>R</I> and 5<I>S</I>)-3-<I>O</I>-Acetyl-5-deoxy-1,2-<I>O</I>-isopropylidene-5-[(methoxy)phenylphosphinyl]-6-<I>O</I>-(tetrahydro-2-pyranyl)-α-D-<I>xylo</I>-hexofuranoses (<B>7</B>) were prepared from 3-<I>O</I>-acetyl-5,6-dideoxy-6-nitro-α-D-<I>xylo</I>-hex-5-enofuranose in 4 steps. Reduction of <B>7</B> 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-<I>O</I>-acetates, whose structures were established by spectroscopy.
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