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- W2023802477 abstract "3,6-Dideoxy-3-C-methyl-2-O-methyl-D-galactopyranose(12) was prepared in 10 steps from methyl 4,6-O-benzylidene-3-deoxy-3-C-methyl-α-D-altropyranoside. 12 was converted into 4,5-di-O-acetyl-3,6-dideoxy-3-C-methyl-2-O-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-O-acetyl-2,4,7-trideoxy-4-C-methyl-1,3-di-O-methyl-D-galacto-1-enoheptitol (16). The treatment of 16 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-C-methyl-3-O-methyl-β-D-galacto-heptopyranoside(19), which then provided the title compound 20 upon Jones oxidation. The potential intermediates, the 1-lithio-1-(methyl 2,4-dideoxy-4-C-methyl-3-O-methyl-α-L-arabino-pentopyranos-5-yl)ethene and (E)-2-(methyl 2,4-dideoxy-4-C-methyl-3-O-methyl-α-L-arabino-pentopyranos-5-yl)propenylcopper intermediates, were prepared from 20 via the corresponding alkenyl iodide and (methyl 2,4-dideoxy-4-C-methyl-3-O-methyl-α-L-arabino-pentopyranos-5-yl)ethyne and were demonstrated to condense with benzaldehyde and ethylene oxide respectively." @default.
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- W2023802477 date "1980-11-01" @default.
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- W2023802477 title "Synthetic Studies of Rifamycins. II. Syntheses of Methyl 2,4,6,7-Tetradeoxy-4-<i>C</i>-methyl-3-<i>O</i>-methyl-α-L-<i>arabino</i>-heptopyranosid-6-ulose and Its Derivatives Utilizable in the Construction of the Rifamycin Ansa Chain Portion" @default.
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- W2023802477 doi "https://doi.org/10.1246/bcsj.53.3252" @default.
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