Synthetic studies of amphotericin B. III. An enantiospecific synthesis of the C-1-C-19 segment of the amphotericin B aglycon.
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概要
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The title compound, (3<I>S</I>,4<I>S</I>,5<I>S</I>,9<I>S</I>,11<I>R</I>,12<I>R</I>,15<I>R</I>,17<I>S</I>)-4-[(<I>t</I>-butyldimethylsilyloxy)methyl]-1,3,5,9,11,12,15,17,19-nonahydroxy-3,5:11,12:15,17-tri-<I>O</I>-isopropylidene-19-<I>O</I>-(4-methoxybenzyl)-9-<I>O</I>-[(2-methoxyethoxy)methyl]-7-nonadecanone (<B>1</B>) was effectively synthesized through the coupling of (3<I>S</I>,5<I>R</I>,8<I>R</I>,9<I>R</I>,11<I>S</I>)-12-iodo-3,5:8,9-di-<I>O</I>-isopropylidene-1-<I>O</I>-(4-methoxybenzyl)-11-<I>O</I>-[(2-methoxyethoxy)methyl]-1,3,5,8,9,11-dodecanehexol (<B>2</B>) and (3<I>S</I>,4<I>R</I>,5<I>S</I>)-4-[(<I>t</I>-butyldimethylsilyloxy)methyl]-3,5-<I>O</I>-isopropylidene-1,1-bis(methylthio)-1-trimethylstannyl-6-heptene-3,5-diol (<B>36</B>). The C-13–C-19 segment <B>36</B> was enantiospecifically synthesized from 1,2:5,6-di-<I>O</I>-isopropylidene-α-D-<I>thero</I>-D-<I>glycero</I>-3-hexofuranosulose (<B>7</B>) via (2<I>S</I>,4<I>R</I>,5<I>S</I>)-5,6-epoxy-3-[(<I>t</I>-butyldimethylsilyloxy)methyl]-1-hexen-3-ol (<B>6a</B>) in 11.6% overall yield.
- 公益社団法人 日本化学会の論文
著者
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Kinoshita Mitsuhiro
Department of Applied Chemistry Engineering Faculty of Keio University
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Morioka Masahiko
Department of Applied Chemistry, Faculty of Science and Technology, Keio University
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Taniguchi Masato
Department of Applied Chemistry, Faculty of Science and Technology, Keio University
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Mizusawa Yasuhiro
Department of Applied Chemistry, Faculty of Science and Technology, Keio University
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Takami Hitoshi
Department of Applied Chemistry, Faculty of Science and Technology, Keio University
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