Collect. Czech. Chem. Commun.
1997, 62, 1776-1798
https://doi.org/10.1135/cccc19971776
Glycosylation of Triterpene Alcohols and Acids of the Lupane and A-Secolupane Series
Eva Klinotováa, Václav Křečeka, Jiří Klinota, Magdalena Endováb, Jana Eisenreichováa, Miloš Buděšínskýb and Martin Štíchaa
a Department of Organic Chemistry, Charles University, 128 40 Prague 2, Czech Republic
b Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic,166 10 Prague 6, Czech Republic
Abstract
A series of 3- and 28-glucosides and glucosyl esters of betulinic acid (1a), 28-hydroxy-3,4-secolupa-4(23),20(29)-dien-3-oic acid (22a), dimethyl ester of 28-hydroxy-2,3-secolup-20(29)-en-2,3-dioic acid (43a), their 20(29)-dihydro derivatives (1b, 22b, 43b) and several other triterpenes of the lupane (12a, 12b) and 3,4-secolupane series (18a, 18b, 32a) has been prepared by reaction of tetra-O-acetyl-α-D-glucopyranosyl bromide in acetonitrile in the presence of mercury(II) cyanide and subsequent deacetylation of the obtained tetra-O-acetyl-β-D-glucopyranosyl derivatives. In several cases attempted glucosylation in the presence of silver silicate afforded predominantly the corresponding 1,2-orthoacetates of α-D-glucopyranose.
Keywords: Lupane; 3,4-Secolupane; 2,3-Secolupane; Betulinic acid; Glucoside; 1H and 13C NMR spectra.
