Glycosylation of Triterpene Alcohols and Acids of the Lupane and A-Secolupane Series

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Title:Glycosylation of Triterpene Alcohols and Acids of the Lupane and A-Secolupane Series
Creators:
Klinotová, Eva
Křeček, Václav
Klinot, Jiří
Endová, Magdalena
Eisenreichová, Jana
Buděšínský, Miloš
Štícha, Martin
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 62, 11, pp. 1776-1798
Uncontrolled Keywords:2,3-Secolupane, Glucoside, Betulinic acid, 3,4-Secolupane, <sup>1</sup>H and <sup>13</sup>C NMR spectra, Lupane

Abstract

A series of 3- and 28-glucosides and glucosyl esters of betulinic acid (<strong>1a</strong>), 28-hydroxy-3,4-secolupa-4(23),20(29)-dien-3-oic acid (<strong>22a</strong>), dimethyl ester of 28-hydroxy-2,3-secolup-20(29)-en-2,3-dioic acid (<strong>43a</strong>), their 20(29)-dihydro derivatives (<strong>1b</strong>, <strong>22b</strong>, <strong>43b</strong>) and several other triterpenes of the lupane (<strong>12a</strong>, <strong>12b</strong>) and 3,4-secolupane series (<strong>18a</strong>, <strong>18b</strong>, <strong>32a</strong>) has been prepared by reaction of tetra-<i>O</i>-acetyl-α-D-glucopyranosyl bromide in acetonitrile in the presence of mercury(II) cyanide and subsequent deacetylation of the obtained tetra-<i>O</i>-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.

Title:Glycosylation of Triterpene Alcohols and Acids of the Lupane and A-Secolupane Series
Creators:
Klinotová, Eva
Křeček, Václav
Klinot, Jiří
Endová, Magdalena
Eisenreichová, Jana
Buděšínský, Miloš
Štícha, Martin
Uncontrolled Keywords:2,3-Secolupane, Glucoside, Betulinic acid, 3,4-Secolupane, <sup>1</sup>H and <sup>13</sup>C NMR spectra, Lupane
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:62
Number:11
Page Range:pp. 1776-1798
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19971776UNSPECIFIED
ID Code:1252
Item Type:Article
Deposited On:06 Feb 2009 17:07
Last Modified:06 Feb 2009 16:08

Citation

Klinotová, Eva; Křeček, Václav; Klinot, Jiří; Endová, Magdalena; Eisenreichová, Jana; Buděšínský, Miloš; Štícha, Martin (1997) Glycosylation of Triterpene Alcohols and Acids of the Lupane and A-Secolupane Series. Collection of Czechoslovak Chemical Communications, 62 (11). pp. 1776-1798. ISSN 0010-0765

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