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Issue 0, 1980
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Syntheses of 1- and 6-S- and 1- and 6-Se-derivatives of 2-amino-2-deoxy-α/β-D-glucopyranose

Abstract

The syntheses of 1,1′-dithiobis-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranose)(6), 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-1-S-dimethylarsino-1-thin-β-D-glucopyranose (7), 2-acetamido-2-deoxy-1-S-dimethylarsino-1-thin-β-D-glucopyranose (8), 2-acetamido-1,3,4-tri-O-acetyl-6-S-acetyl-2-deoxy-6-thio-α-D-glucopyranose (11), 6,6′-dithiobis-(2-acetamido-1,3,4-tri-O-acetyl-2-deoxy-α-D-glucopyranose)(12), 2-acetamido-1,3,4-tri-O-acetyl-2-deoxy-6-S-dimethylarsino-6-thin-α-D-glucopyranose (13), 1,1′-diselenobis-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranose)(17), 2-Se-(2-acetamido-1,3,4-tri-O-acetyl-2-deoxy-α-D-glucopyranosyl)-3-(NN-dimethyl)selenoisourea hydroiodide (19), and 6,6′-diselenobis-(2-acetamido-1,3,4-tri-O-acetyl-2-deoxy-α-D-glucopyranose)(20) are discussed. N.m.r. and mass spectral properties of the compounds are described. The rearrangement of 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucosyl chloride in acetone to 1,3,4,6-tetra-O-acetyl-α-D-glucosamine hydrochloride is reported. The α- and β-anomers of the basic amino-sugar compounds have been characterized and discrepancies with previous reports have been noted.

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Article type: Paper
DOI: 10.1039/P19800002287
J. Chem. Soc., Perkin Trans. 1, 1980, 2287-2293

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    Syntheses of 1- and 6-S- and 1- and 6-Se-derivatives of 2-amino-2-deoxy-α/β-D-glucopyranose

    G. C. Chen, C. H. Banks, K. J. Irgolic and R. A. Zingaro, J. Chem. Soc., Perkin Trans. 1, 1980, 2287
    DOI: 10.1039/P19800002287

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