Synthesis of Di-<I>N</I>-acetyl-di-<I>N</I>-benzyloxycarbonyl-<I>O</I>-cyclohexylidenestreptidine
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概要
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Reaction of streptidine with excess benzyloxycarbonyl chloride, followed by partial alkaline hydrolysis, gave di-<I>N</I>-benzyloxycarbonylstreptidine (<B>1</B>), which, by treatment with 3,4-dihydro-2<I>H</I>-pyran, gave a tetra-<I>O</I>-tetra-hydropyranyl derivative (<B>3</B>). Acetylation of <B>3</B> then gave a di-<I>N</I>-acetyl derivative (<B>4</B>), which was, after removal of the tetrahydropyranyl groups, allowed to react with 1,1-dimethoxycyclohexane to furnish di-<I>N</I>-acetyl-di-<I>N</I>-benzyloxycarbonyl-<I>O</I>-cyclohexylidenestreptidine (<B>6</B>). This is the first preparation of a useful intermediate for the synthesis of streptidine glycosides.
- 公益社団法人 日本化学会の論文
著者
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Umezawa Sumio
Department of Applied Chemistry Engineering Faculty Keio University
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Tsuchiya Tsutomu
Department of Applied Chemistry, Faculty of Engineering, Keio University
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Takahashi Yoshikazu
Department of Applied Chemistry, Faculty of Engineering, Keio University
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