HYDROGENOLYSIS OF CARBOHYDRATES: V. ISOMERIZATION OF METHYL β-L-ARABOPYRANOSIDE
- 1 June 1958
- journal article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 36 (6) , 921-925
- https://doi.org/10.1139/v58-133
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.Keywords
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