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- W2022504169 abstract "Two routes for the synthesis of 6-O-(2-acetamido-2-deoxy-β-D-glucopyranosyluronic acid)-D-glucose (12) were studied. In the first, benzyl 6-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-β-D-glucopyranoside (10) was obtained by condensation of benzyl 2,3,4-tri-O-acetyl-β-D-glucopyranoside (obtained via the 6-O-trityl derivative) with 3,4,6-tri-O-acetyl-2-deoxy-2-diphenylphosphorylamino-α-D-glucopyranosyl bromide, followed by removal of the diphenylphosphoryl and O-acetyl groups and subsequent N-acetylation. In the second route, 2-methyl-4,5-(3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyrano)-2-oxazoline was used as 2-acetamido-2-deoxy-D-glucose moiety in the condensation reaction to give benzyl 6-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-2,3,4-tri-O-acetyl-β-D-glucopyranoside (11), and subsequent removal of O-acetyl groups gave compound 10. Oxidation of the primary hydroxyl group of 10 gave benzyl 6-O-(2-acetamido-2-deoxy-β-D-glucopyranosyluronic acid)-β-D-glucopyranoside (8), which was converted by catalytic hydrogenolysis into the free disaccharide 12." @default.
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- W2022504169 date "1972-09-01" @default.
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- W2022504169 title "The synthesis of 6-O-(2-acetamido-2-deoxy-β-D-glucopyranosyluronic acid)-D-glucose" @default.
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- W2022504169 doi "https://doi.org/10.1016/s0008-6215(00)82266-1" @default.
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