Total synthesis of aminoglycoside antibiotics, apramycin and saccharocin (KA-5685).
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概要
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Apramycin and saccharocin (KA-5685) have been synthesized from previously synthesized neamine (<B>3</B>). Addition of allylmagnesium chloride to 4-<I>O</I>-[3′,4′-<I>O</I>-cyclohexylidene-2′-deoxy-2′-(tosylamino)-α-D-<I>gluco</I>-hexodialdo-1′,5′-pyranosyl]-5,6-<I>O</I>-cyclohexylidene-1,3-di-<I>N</I>-tosyl-2-deoxystreptamine which was derived from <B>3</B> through the 6′-<I>N</I>-oxide, gave 4-<I>O</I>-[3′,4′-<I>O</I>-cyclohexylidene-2′,7′,8′,9′-tetradeoxy-2′-(tosylamino)-L-<I>glycero</I>- and D-<I>glycero</I>-α-D-<I>gluco</I>-non-8′-enopyranosyl]-5,6-<I>O</I>-cyclohexylidene-1,3-di-<I>N</I>-tosyl-2-deoxystreptamines which were in turn converted into 4-<I>O</I>-[(8′<I>S</I>)-7′-<I>N</I>,6′-<I>O</I>-carbonyl-2′,3′,7′-trideoxy-8′-<I>O</I>-methyl-7′-(methylamino)-2′-(tosylamino)-D-<I>glycero</I>-α-D-<I>allo</I>-octodialdo-1′,5′:8′,4′-dipyranos-1′-yl]-5,6-<I>O</I>-cyclohexylidene-1,3-di-<I>N</I>-tosyl-2-deoxystreptamine (<B>25</B>), <I>via</I> azidonitration of 1-<I>N</I>-acetyl-4-<I>O</I>-[3′,6′-di-<I>O</I>-acetyl-4′,8′-anhydro-2′,7′-dideoxy-2′-(tosylamino)-L-<I>glycero</I>-α-D-<I>gluco</I>-oct-7′-enopyranos-1′-yl]-5,6-<I>O</I>-cyclohexylidene-1,3-di-<I>N</I>-tosyl-2-deoxystreptamine and epimerization of the 6′-hydroxyl group. Successive deprotection of <B>25</B> afforded aprosamine, from which 1,2′,3,7′-tetrakis(<I>N</I>-benzyloxycarbonyl)aprosamine (<B>28</B>) was prepared, and glycosidation of <B>28</B> with 4-azido-2,3,6-tri-<I>O</I>-benzyl-4-deoxy-β-D-glucopyranosyl fluoride or 2,3,4,6-tetra-<I>O</I>-benzyl-β-D-glucopyranosyl fluoride, followed by hydrogenolysis, completed the total synthesis.
- 公益社団法人 日本化学会の論文
著者
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Tatsuta Kuniaki
Department Of Applied Chemistry Faculty Of Science And Technology Keito University
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Takahashi Hideaki
Department Of Biology And Function In Head And Neck Yokohama City University Graduate School Of Medicine
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Kinoshita Mitsuhiro
Department of Applied Chemistry Engineering Faculty of Keio University
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Akimoto Kohji
Department of Applied Chemistry, Faculty of Science and Technology, Keio University
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Hamatsu Takao
Department of Applied Chemistry, Faculty of Science and Technology, Keio University
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Annaka Masahiko
Department of Applied Chemistry, Faculty of Science and Technology, Keio University
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