目的 設計合成齊墩果酸和熊果酸C₃、C₂₈ 衍生物.方法 先將葡萄糖和半乳糖通過Schmidit 法制備三氯乙酰亞胺酯糖給體;然后分別以齊墩果酸和熊果酸為起始原料,經芐基保護,再進行糖苷化、芐基脫保護、酰胺化、苯甲?；摫Ｗo,得到10 個酰胺衍生物F₁～F₁₀.其中F₁、F₃ 通過四甲基哌啶氧化物(TEMPO)及NaClO/NaClO₂ 氧化體系得到糖醛酸化合物F₁₁、F₁₂.結果 合成了5 個熊果酸C₃ 位葡萄糖苷C₂₈ 位酰胺衍生物、5 個齊墩果酸C₃ 位半乳糖苷C₂₈ 位酰胺衍生物及2個熊果酸C₃ 位葡萄糖醛酸苷C₂₈ 位酰胺衍生物,并分別通過¹H-NMR、¹³C-NMR 和MS 確認結構.結論 12 個化合物均未見報道,為三萜皂苷的構效關系及生物活性研究奠定基礎.

Objective To design and synthesize the derivatives of oleanolic acid and ursolic acids C₃ and C₂₈. Methods First, glucose and galactose trichloroacetimidates donors were prepared with glucose and galactose by Schmidit method. Then oleanolic acid and ursolic acid were used as starting material to synthesize 10 target compounds F₁-F₁₀ by the benzyl protection, glycosylation, benzyl deprotection, amidation, and benzoyl deprotection. Iduronate compounds F₁₁ and F₁₂ were obtained from compounds F₁ and F₃ correspondingly via the TEMPO and NaClO/NaClO₂ oxidation system. Results Five 3-glucoside-28-amid triterpenoid saponins derivatives, five 3-galactoside- 28-amid triterpenoid saponins derivatives, and two 28-amid-3-O-glucuronic acid ursolic derivatives were obtained. All compounds were confirmed by the application of ¹H-NMR, ¹³C-NMR, and MS. Conclusion Twelve compounds are synthesized for the first time, which lays the foundation for the structure-function relationship and bioactivity studies of triterpenoid saponins.

北京市自然科學基金資助項目(7144225)