天然产物 3-O-(4'-O-acetyl)-α-L-arabinopyranosyloleanolic acid 的合成
Synthesis of natural saponin 3-O-(4'-O-acetyl)-α-L-arabinopyranosyloleanolic acid
丁绍越 1焉玉超 1张连哲 1刘洋1
作者信息
- 1. 沈阳药科大学 基于靶点的药物设计与研究教育部重点实验室,辽宁沈阳 110016
- 折叠
摘要
目的 研究具有天然抗肿瘤活性的齐墩果酸皂苷类化合物3-O-(4'-O-acetyl)-α-L-arabinopyranosylolea-nolic acid的化学合成方法.方法 先合成齐墩果酸苄酯和全苯甲酰化保护的阿拉伯糖三氯乙酰亚胺酯,将上述两个片段经糖苷化反应并脱去苯甲酰基,再经适宜的保护基策略、乙酰化反应、脱去苄基保护基得到目标化合物.结果 与结论成功合成了目标化合物,并开发了一种较高收率的选择性合成乙酰化阿拉伯糖4位羟基的方法,为合成具有类似结构片段的化合物提供了新的思路.
Abstract
The chemical synthesis of a natural oleanolic acid saponin compound 3-O-(4'-O-acetyl)-α-L-arabinopyranosyloleanolic acid was reported,which was isolated from Garcinia hanburyi Hook.f.and had good antitumor activity.The target compound was obtained by glycosidation,removal of benzoyl groups,and then by a suitable"protection"strategy,acetylation and removal of the benzyl group.A method for selective acetylation of the hydroxyl group at the 4-position of arabinose was established with high yield,which could provide a new method for the construction of selective acetylation of compounds with polyhydroxyl structure.
关键词
齐墩果酸/抗肿瘤/阿拉伯糖/天然皂苷/乙酰化Key words
oleanolic acid/antitumor/arabinose/natural saponin/acetylation引用本文复制引用
出版年
2024
NETL
NSTL
万方数据