Abstract
DURING recent years, a series of papers from this laboratory have shown that derivatives of glucose may be converted smoothly into derivatives of altrose, galactose and gulose by means of optical inversion within the molecule1. In each case the key substance to such a conversion has been an anhydro-compound of the ethylene oxide type in which the ring is broken under the influence of alkali. For example, 2: 3-anhydro 4: 6-benzylidene α-methylalloside or 2: 3-anhydro 4: 6-benzylidene α-methylmannoside, in our experience, invariably yield derivatives of altrose when treated with alcoholic caustic potash or sodium methoxide solution.
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References
Mathers and Robertson, J. Chem. Soc., 1076 (1933); Robertson and Griffith, J. Chem. Soc., 1193 (1935); Oldham and Robertson, J. Chem. Soc., 685 (1935).
Ber., 53, 541 (1920).
Ber., 59, 714 (1926).
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ROBERTSON, G., MYERS, W. & TETLOW, W. “Methyl Epiglucosamine” and 2-Amino α-Methyl-altroside. Nature 142, 1076–1077 (1938). https://doi.org/10.1038/1421076b0
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DOI: https://doi.org/10.1038/1421076b0
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