Synthesis of a masked derivative of 3'-deoxydihydrostreptobiosamine, a precursor for the synthesis of 3"-deoxydihydrostreptomycin.
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概要
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2′-<I>N</I>-Acetyl-4′,6′-di-<I>O</I>-acetyl-3,3a-<I>O</I>-carbonyl-3′-deoxydihydrostreptobiosamine (<B>15</B>), a precursor in the synthesis of 3″-deoxydihydrostreptomycin, was prepared from benzyl α-dihydrostreptobiosaminide. The synthesis involves formation of L-allo compound (<B>5</B>) with inversion of the 3′-hydroxyl group of L-gluco derivative (<B>2</B>) in order to facilitate 3′-chlorination, dechlorination, of the 3′-chloro-L-gluco derivative (<B>7</B> or <B>11</B>) with tributyltin hydride, and utilization of cyclic 3,3a-<I>O</I>-carbonyl group instead of 3,3a-<I>O</I>-isopropylidene group which was unstable in the later reactions.
- 公益社団法人 日本化学会の論文
著者
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Kobayashi Shigeru
Deparment Of Oral Anatomy Kyushu Dental College
-
Tsuchiya Tsutomu
Institute of Bioorganic Chemistry
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Umezawa Sumio
Institute of Bioorganic Chemistry
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Umezawa Hamao
Institute of Bioorganic Chemistry
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Sano Hiroshi
Institute of Bioorganic Chemistry
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