Synthesis of two bidesmosidic ursolic acid saponins bearing a 2,3-branched trisaccharide residue.
The focus of this work was on the synthesis of two bidesmosidic ursolic acid saponins bearing a 2,3-branched trisaccharide residue. Therefore, 3-O-{[beta-D-glucopyranosyl-(1-->2)]-[alpha-L-arabinopyranosyl-(1-->3)]-alpha-L-arabinopyranosyl}ursolic acid-28-O-[beta-D-glucopyranosyl] ester 1 was concisely synthesized by two strategies in 22% and 41% overall yield, respectively, and another congener 3-O-{[beta-D-xylopyranosyl-(1-->2)]-[beta-D-glucopyranosyl-(1-->3)]-alpha-L-arabinopyranosyl}ursolic acid-28-O-[beta-D-glucopyranosyl] ester 2 was also efficiently prepared in 81% overall yield. The (1)H NMR and (13)C NMR signals of saponin 2 are all consistent with those reported for the natural product.
Wang
Peng
P
Key Laboratory of Marine Drugs, Ministration of Education, Marine Drug and Food Institute, Ocean University of China, Qingdao.
Li
Chunxia
C
Zang
Jing
J
Song
Ni
N
Zhang
Xiuli
X
Li
Yingxia
Y
D002240:Carbohydrate Sequence; D006031:Glycosylation; D008969:Molecular Sequence Data; D025942:Oligosaccharides, Branched-Chain / Q000737:chemistry*; D012503:Saponins / Q000138:chemical synthesis*; D014312:Trisaccharides / Q000737:chemistry*; D014315:Triterpenes / Q000737:chemistry*; D000097245:Ursolic Acid
D025942:Oligosaccharides, Branched-Chain; D012503:Saponins; D014312:Trisaccharides; D014315:Triterpenes; D000097245:Ursolic Acid