Synthesis of two natural oleanolic acid saponins
Synthesis of two natural oleanolic acid saponins
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DOI：
10.1002/cjoc.200690098
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发表时间：
2006-04-01
影响因子：
5.4
通讯作者：
Li, YX
中科院分区：
文献类型：
--
作者：
Li, CX;Zang, J;Li, YX
采用聚合策略合成了3- o -[ss- d-葡萄糖吡喃基-(1 -> 3)- α - l-阿拉伯葡萄糖吡喃基]-齐墩果酸-28- o -[ss- d-葡萄糖吡喃基]酯1。采用分步法合成皂素2,3 -o -{[ss- d-葡萄糖吡喃基-(1 -> 2)]-[α - l-阿拉伯糖吡喃基-(1 -> 3)]- α - l-阿拉伯糖吡喃基}-齐墩果酸-28- o -（ss- d-葡萄糖吡喃基）酯，观察到阿拉伯糖基末端残基为C-1(4)构象而非典型的C-4(1)构象的异常现象。脱保护或加热均不能恢复正常构象，导致产物2′不2。
3-O-[ss-D-Glucopyranosyl-(1 -> 3)-alpha-L-arabinopyranosyl]-oleanolic acid-28-O-[ss-D-glucopyranosyl] ester 1 was synthesized concisely by a convergent strategy. Using stepwise fashion for the synthesis of saponin 2, 3-O-{[ss-D-glucopyranosyl-(1 -> 2)]-[alpha-L-arabinopyranosyl-(1 -> 3)]-alpha-L-arabinopyranosyl}-oleanolic acid-28-O-(ss-D-glucopyranosyl) ester, an abnormal phenomenon, that the terminal arabinosyl residue took the C-1(4) conformation instead of typical C-4(1) form, was observed. Deprotection or heating could not resume the normal conformation, which resulted in the product of 2 ' not 2.