Abstract
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-{[β-d-glucopyranosyl-(1→2)]-[α-l-arabinopyranosyl-(1→3) ]-α-l-arabinopyranosyl}ursolic acid-28-O-[β-d-glucopyranosyl] ester 1 was concisely synthesized by two strategies in 22% and 41% overall yield, respectively, and another congener 3-O-{[β-d-xylopyranosyl-(1→2)]- [β-d-glucopyranosyl-(1→3)]-α-l-arabinopyranosyl}ursolic acid-28-O-[β-d-glucopyranosyl] ester 2 was also efficiently prepared in 81% overall yield. The 1H NMR and 13C NMR signals of saponin 2 are all consistent with those reported for the natural product.
Original language | English |
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Pages (from-to) | 2086-2096 |
Number of pages | 11 |
Journal | Carbohydrate Research |
Volume | 340 |
Issue number | 13 |
DOIs | |
State | Published - 26 Sep 2005 |
Externally published | Yes |
Keywords
- Glycosylation
- Saponin
- Synthesis
- Ursolic acid