Abstract
A convenient method is proposed for the synthesis of all the individual methyl ethers of methyl 2-acetamido-2-deoxy-α-D-glucopyranoside based on the partial methylation of 2-acetamido-2-deoxy-α-D-glucopyranoside with dimethyl sulfate in an alkaline medium followed by preparative liquid column chromatography on silica gel of the resulting mixture of methyl ethers.
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Literature cited
R. W. Jeanloz, Adv. Carbohydr. Chem.,13, 189 (1958).
J. E. Cadotte, F. Smith, and D. Spriestersbath, J. Am. Chem. Soc.,74, 1501 (1952).
A. S. Shashkov, A. Yu. Evstigneev, and V. A. Derevitskaya, Bioorg. Khim.,4, 1495 (1978).
W. O. Cutler, W. N. Haworth, and S. J. Peat, J. Chem. Soc., 1979 (1937).
W. Roth and W. Pigman, J. Am. Chem. Soc.,82, 4608 (1960).
R. W. Jeanloz and C. Gansser, J. Am. Chem. Soc.,79, 2583 (1957).
R. W. Jeanloz, J. Am. Chem. Soc.,76, 558 (1954).
R. W. Jeanloz, J. Am. Chem. Soc.,74, 4597 (1952).
R. W. Jeanloz, J. Am. Chem. Soc.,76, 555 (1954).
R. Kuhn, F. Zillikine, and A. Gauhe, Chem. Ber.,86, 466 (1953).
W. H. Meyers and G. J. Robertson, J. Am. Chem. Soc.,65, 8 (1943).
Additional information
Pacific Ocean Institute of Bioorganic Chemistry, Far Eastern Scientific Center, USSR Academy of Sciences, Vladivostok. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 787–790, November–December, 1987.
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Evtushenko, E.V., Plisova, E.Y. & Ovodov, Y.S. Synthesis of methyl ethers of methyl 2-acetamido-2-deoxy-α-D-glucopyranoside. Chem Nat Compd 23, 651–653 (1987). https://doi.org/10.1007/BF00596634
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DOI: https://doi.org/10.1007/BF00596634