Orthoesters of sugars

Autor: Bochkov, A. F., Betaneli, V. I., Kochetkov, N. K.
Zdroj: Russian Chemical Bulletin; June 1974, Vol. 23 Issue: 6 p1299-1304, 6p
Abstrakt: 1.On the example of the methyl- and cyclohexylorthoacetates of glucopyranose it was shown that the glycosylation of alcohols with the orthoesters of sugars is accompanied by a side reaction that leads to the formation of the anomeric glycosides with a free hydroxyl at C-2 and a predominance of thea-anomer. In this reaction the orthoester group is removed as the alkyl acetate.2.Data were obtained which indicate that the glycosylation of the alcohol by the orthoester precedes the rapid reversible transesterification step, with exchange of the alkoxyl moieties between the alcohol and the orthoester.
Databáze: Supplemental Index