Mode of cleavage of the c-c bonds in methyl pento- and hexo-pyranosides with periodate
1979; Elsevier BV; Volume: 68; Issue: 1 Linguagem: Inglês
10.1016/s0008-6215(00)84057-4
ISSN1873-426X
AutoresSusumu Honda, Noriko Hamajima, Kazuaki Kakehi,
Tópico(s)Analytical Chemistry and Chromatography
ResumoAbstract The course of oxidation reactions of three methyl pentopyranosides and five methyl hexopyranosides with periodate was studied by simultaneous determination of the conjugated aldehydes in the products. It was found that the C-3-C-4 bonds in all of these glycosides were cleaved rapidly, but the velocity of subsequent cleavage of the C-2-C-3 bonds depended on the configuration of the substituent groups on the pyranose ring. Equatorial C-1 methoxyl and C-2 hydroxyl groups favored cleavage of the C-2-C-3 bonds more than did the corresponding axial groups, whereas the equatorial C-5 hydroxymethyl group suppressed C-2-C-3-bond-cleavage. The 4-isomeric glycosides were oxidized at the same rate, without regard to the configuration at C-4.
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