| 殷文俊,王军林,孙鹏,等.金催化甘露糖-b-(1→6)-甘露糖-b-(1→6)-葡萄糖三糖的合成[J].中国海洋药物,2016,35(5):69-73. |
| 金催化甘露糖-b-(1→6)-甘露糖-b-(1→6)-葡萄糖三糖的合成 |
| Gold(I)-Catalyzed Synthesis of b-Man-(1→6)-b-Man-(1→6)-b-Glu Trisaccharide |
| 投稿时间：2016-03-07 修订日期：2016-04-26 |
| DOI： |
| 中文关键词: 金催化 b-甘露糖苷键 甘露糖邻己炔基苯甲酸酯 |
| English Keywords:gold catalyzed b-mannosidic bond mannosyl ortho-hexynylbenzoate |
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| 中文摘要: |
| 目的 利用金催化立体选择性构建b-甘露糖苷键的方法高效合成甘露糖-b-(1→6)-甘露糖-b-(1→6)-葡萄糖三糖。方法 以4,6-O-苄叉保护的甘露糖邻己炔基苯甲酸酯3为供体,在Au(I) 复合物和银盐催化下,与葡萄糖受体4反应,得到二糖产物5；二糖5在Bu2BOTf/BH3.THF条件下,将苄叉选择性还原开环至6-羟基,得到二糖受体6,进而再与糖基供体3反应,得到三糖2。 结果 分别以90%的产率、b/a = 14.2/1的选择性得到二糖5和88%的产率、b/a = 15.9/1的选择性得到三糖2。 |
| English Summary: |
| Objective A b-Man-(1→6)-b-Man-(1→6)-b-Glu trisaccharide block was synthesized with excellent yield via gold(I)-catalyzed stereoselective construction of b-mannosidic bond. Method The 4,6-O-benzylidene tethered mannosyl ortho-hexynylbenzoate 3 was used as glycosyl donor which reacted with glucose acceptor 4 catalyzed by Au(I) complex and Ag salt to give disaccharide 5. Then regioselective reductive ring opening of benzylidene acetal in disaccharide 5 to the 6-hydroxyl product 6 was conducted in the presence of Bu2BOTf/BH3.THF, which reacted with glycosyl donor 3 to give the trisaacharide 2. Results The disaccharide 5 and trisaacharide 2 were achieved in 90%, b/a = 14.2/1 and 88%, b/a = 15.9/1, respectively. |
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