Conclusions
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1.
When CrO3 in AcOH or Ac2O acts on methylated methyl glycopyranosides with an axial proton at C1 the glycoside center is initially subjected to the attack. The predominant direction of the subsequent course of the oxidation depends on the nature of the C5 substituent on the pyranose ring: The oxidative splitting of the C1-C2 bond is characterixtic of hexosides, and the oxidative splitting of the C1-O5 bond is characteristic of the 6-deoxyhexosides and pentopyranosides.
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2.
In the case of the oxidation of methyl α-D-hexopyranosides under the same conditions, the attack of the CrO3 is directed at the CH3O groups. This oxidizes them to formyl groups. The group at C6 is preferentially oxidized in AcOH, while a mixture of all the possible mono- and di-O-formyl derivatives forms in Ac2O.
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Research assistant, Academy of Sciences of the Hungarian Peoples Republic.
Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 3, pp. 635–643, March, 1976.
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Kochetkov, N.K., Chizhov, O.S., Sviridov, A.F. et al. Oxidation of completely methylated methyl glycopyranosides by chromic anhydride. Russ Chem Bull 25, 619–625 (1976). https://doi.org/10.1007/BF01106666
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DOI: https://doi.org/10.1007/BF01106666