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- W1495509211 abstract "The methyl ethers of ethyl 2-deoxy-2-(2,4-dinitroanilino)-α-d-glucopyranoside (2) and the corresponding free sugar (1) have been synthesised. They are crystalline and are readily separated and identified chromatographically. Their structures were established by definitive synthesis, interconversion, and periodate-oxidation studies. The 4- (10) and 6- (11) methyl ethers were synthesised via ethyl 3,4-di-O-acetyl-2-deoxy-2-(2,4-dinitroaniline)-6-O-trityl-α-d-glucopyranoside (3) and its de-O-tritylated derivative (7). When 7 was methylated, the acetyl group at C-4 migrated to C-6 (76%). The C-3 acetyl group in the 3,6-di-O-acetyl-4-O-methyl derivative 6 underwent methanolysis and acid hydrolysis abnormally slowly. The 3,6-di- and the 4,6-dimethyl ethers, 12 and 13, were synthesised by graded methylation of the 4- and 6-monoethers, 10 and 11. The 3-methyl ether 17 was synthesised via ethyl 4,6-O-benzylidene-2-deoxy-2-(2,4-dinitroanilino)-α-d-glucopyranoside (15), and the 3,4-dimethyl ether 20 was obtained by hydrolysis of the product of methylation of ethyl 2-deoxy-2-(2,4-dinitroanilino)-6-O-trityl-α-d-glucopyranoside (18). The 3,4,6-trimethyl ether 14 was obtained by methylation of glycoside 2." @default.
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- W1495509211 date "1969-04-01" @default.
- W1495509211 modified "2023-10-17" @default.
- W1495509211 title "Aminosaccharides" @default.
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- W1495509211 doi "https://doi.org/10.1016/s0008-6215(00)80032-4" @default.
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