| Abstract | Treatment of methyl β-L-arabopyranoside under hydrogenolytic conditions with copper chromium oxide catalyst induces extensive isomerization. Products formed include glycosides of D-ribose, D-xylose, D-lyxose, and L-lyxose which together represent about an 80–90% conversion of starting material. Isolation of these compounds shows that carbons 2, 3, and 4 undergo isomerization, but no evidence has been obtained of anomerization. These findings possibly explain the formation of an optically inactive mixture of cis- and trans-tetrahydropyran-3,4-diol under slightly more drastic reaction conditions. |
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