Synthetic studies of rifamycins. II. Syntheses of methyl 2,4,6,7-tetradeoxy-4-C-methyl-3-O-METHYL-.ALPHA.-L-arabino-heptopyranosid-6-ulose and its derivatives utilizable in the construction of the rifamycin ansa chain portion.
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概要
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3,6-Dideoxy-3-<I>C</I>-methyl-2-<I>O</I>-methyl-D-galactopyranose(<B>12</B>) was prepared in 10 steps from methyl 4,6-<I>O</I>-benzylidene-3-deoxy-3-<I>C</I>-methyl-α-D-altropyranoside. <B>12</B> was converted into 4,5-di-<I>O</I>-acetyl-3,6-dideoxy-3-<I>C</I>-methyl-2-<I>O</I>-methyl-D-galactose, which was then condenced in ether with (methoxymethylene)triphenylphosphorane (generated from the phosphonium salt with the dimethylsulfinylmethanide anion in ether) to produce 5,6-di-<I>O</I>-acetyl-2,4,7-trideoxy-4-<I>C</I>-methyl-1,3-di-<I>O</I>-methyl-D-<I>galacto</I>-1-enoheptitol (<B>16</B>). The treatment of <B>16</B> with NBS in methanol, followed by the debromination of the resulting 2-bromo aldehyde dimethyl acetal with tributylstannane, deacetylation, and mild methanolysis afforded methyl 2,4,7-trideoxy-4-<I>C</I>-methyl-3-<I>O</I>-methyl-β-D-<I>galacto</I>-heptopyranoside(<B>19</B>), which then provided the title compound <B>20</B> upon Jones oxidation. The potential intermediates, the 1-lithio-1-(methyl 2,4-dideoxy-4-<I>C</I>-methyl-3-<I>O</I>-methyl-α-L-<I>arabino</I>-pentopyranos-5-yl)ethene and (<I>E</I>)-2-(methyl 2,4-dideoxy-4-<I>C</I>-methyl-3-<I>O</I>-methyl-α-L-<I>arabino</I>-pentopyranos-5-yl)propenylcopper intermediates, were prepared from <B>20</B> <I>via</I> the corresponding alkenyl iodide and (methyl 2,4-dideoxy-4-<I>C</I>-methyl-3-<I>O</I>-methyl-α-L-<I>arabino</I>-pentopyranos-5-yl)ethyne and were demonstrated to condense with benzaldehyde and ethylene oxide respectively.
- 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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Kinoshita Mitsuhiro
Department of Applied Chemistry Engineering Faculty of 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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Nakata Masaya
Department of Applied Chemistry, Faculty of Engineering, Keio University
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