Synthetic studies of rifamycins. IV. The synthesis of rifamycin ansa-chain compound using carbohydrate.
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概要
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3-<I>O</I>-Benzyl-2,4,7-trideoxy-5,6-<I>O</I>-isopropylidene-2,4-di-<I>C</I>-methyl-L-<I>glycero</I>-D-<I>galacto</I>-heptose (<B>6</B>) was synthesized through 16 steps from 4,6-<I>O</I>-benzylidene-3-deoxy-3-<I>C</I>-methyl-α-D-altropyranoside (<B>7</B>). The condensation of <B>6</B> with methyl 2,4,6,7-tetradeoxy-6-lithio-4-<I>C</I>-methyl-3-<I>O</I>-methyl-α-L-<I>arabino</I>-(<I>E</I>)-6-heptenopyranoside, derived from <B>7</B>, afforded a mixture (<B>25</B>) of methyl 9-<I>O</I>-benzyl-2,4,6,8,10,13-hexadeoxy-11,12-<I>O</I>-isopropylidene-4,8,10-tri-<I>C</I>-methyl-3-<I>O</I>-methyl-6-methylene-L-<I>glycero</I>-D-<I>galacto</I>-β-D-<I>galacto</I>-tridecopyranoside and its α-L-<I>altro</I> epimer in a 61% yield. The debenzylation of <B>25</B> by hydrogenolysis with palladium black, followed by homogeneous hydrogenation with tris(triphenylphosphine)chlororhodium(I) and the chromatographic isolation of the desired diastereomer, gave, after acetylation, methyl 7,9-di-<I>O</I>-acetyl-2,4,6,8,10,13-hexadeoxy-11,12-<I>O</I>-isopropylidene-4,6,8,10-tetra-<I>C</I>-methyl-3-<I>O</I>-methyl-L-<I>threo</I>-L-<I>manno</I>-β-D-<I>galacto</I>-tridecopyranoside-(1,5) (<B>3</B>) in a 19% yield. The hydrolysis of <B>3</B> followed by periodate oxidation and Wittig condensation with (methoxycarbonylmethylene)triphenylphosphorane, affords in a 79% yield, methyl [methyl 7,9-di-<I>O</I>-acetyl-2,4,6,8,10,11,12-heptadeoxy-4,6,8,10-tetra-<I>C</I>-methyl-3-<I>O</I>-methyl-L-<I>manno</I>-β-D-<I>galacto</I>-(<I>E</I>)-11-tridecenopyranosid]uronate, which is convertible into the title compound.
- 公益社団法人 日本化学会の論文
著者
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Nakata Masaya
Department Of Applied Chemistry Faculty Of Science And Technology Keio University
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Sakai Toshiya
Department of Chemical Engineering, Kyushu University
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Takao Hideaki
Department Of Chemistry Faculty Of Science Okayama University
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Tatsuta Kuniaki
Department Of Applied Chemistry Faculty Of Science And Technology Keito University
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Kinoshita Mitsuhiro
Department of Applied Chemistry Engineering Faculty of Keio University
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Tatsuta Kuniaki
Department of Applied Chemistry, Faculty of Engineering, Keio University
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Ikeyama Yutaka
Department of Applied Chemistry, Faculty of Engineering, Keio University
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Takao Hideaki
Department of Applied Chemistry, Faculty of Engineering, Keio University
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Sakai Toshiya
Department of Applied Chemistry, Faculty of Engineering, Keio University
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