Five 11-deoxoglycyrrhetinic acid 3-monodesmosides were synthesized and the bacteriostatic activities were studied. Before the glycosylation, benzoyl glycoyl trichloroacetimidates were synthesized as donors, then, 3-OH of acetyl 11-deoxoglycyrrhetinate was coupled as glycosyl-receptors with the donors through glycosylation method at the promotion of trimethylsilyl trifluoromethanesulphonate (TMSOTf) to afford 5 benzoyl glycosyl derivatives of acetyl 11-deoxoglycyrrhetinate 7a～7e. Deprotection of the derivatives afforded acetyl 11-deoxoglycyrrhetinate 3-monodesmoside 8a～8e. The structures all compounds were characterized by 1H NMR, MS and Ultimate analysis. The preliminary pharmacological research showed that compound 8a could protect the growth of E. col while 8e could protect the growth of Bacillus subtilis and yeast at high level of N,N-dimethylformamide (DMF).
WANG Jun
,
WEN Wei-He
,
HU Xiao-Li
,
ZHU Yu-Liang
. Synthesis and Activity of 11-Deoxoglycyrrhetinic Acid 3-Monodesmosides[J]. Chinese Journal of Organic Chemistry, 2012
, 32(01)
: 138
-144
.
DOI: 10.6023/cjoc1104084
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