| 李发荣,吕昌仑,曹爽,等.海洋糖脂Erylusamine B四糖片段的合成研究[J].中国海洋药物,2024,43(5):17-27. |
| 海洋糖脂Erylusamine B四糖片段的合成研究 |
| Synthesis of tetrasaccharide fragment of marine glycolipid Erylusamine B |
| 投稿时间：2023-04-07 修订日期：2023-05-23 |
| DOI：10.13400/j.cnki.cjmd.2024.05.010 |
| 中文关键词: 糖脂 Erylusamine B 糖苷化 四糖 |
| English Keywords:Glycolipid Erylusamine B Glycosylation tetrasaccharide |
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| 中文摘要: |
| 对海洋糖脂Erylusamine B的四糖片段进行合成研究，旨在为Erylusamine B的全合成及构效关系研究奠定基础。方法：以D-木糖为原料，通过7步反应以25.1%的产率制备了2-OH裸露的木糖受体6，经6步反应以55.3%的产率制备了4-OH裸露的木糖受体11；以全乙酰化的阿拉伯糖硫苷为原料，通过两步反应以87%的产率合成了三氯乙酰亚胺酯供体13，通过4步反应以59%的产率合成了硫苷供体16；供体13和木糖受体11进行糖苷化反应合成Ara-α-(1→4)-Xyl二糖17；硫苷供体16和木糖受体6经糖苷化反应合成Ara-α-(1→2)-Xyl二糖19; 二糖供体17和二糖受体19经NIS/TMSOTf催化顺利合成四糖20。结果：通过[2+2]汇聚式合成策略以83%的糖苷化产率得到Ara-α-(1→4)-Xyl-β-(1→3)-[Ara-α-(1→2)]-Xyl四糖产物（20），为海洋糖脂Erylusamine B的合成提供物质基础和技术手段。 |
| English Summary: |
| Abstract: Objective The tetrasaccharide fragment of marine glycolipid Erylusamine B was synthesized for the total synthesis of Erylusamine B and biological activity in future. Methods xylose receptors 6 and 11 were synthesized from D-xylose with overall yields of 25.1% and 55.3% respectively; arabinose trichloroacetimidate donor 13 and thiolglycoside donor 16 were synthesized from p-Tolyl-2,3,4-tri-O-acetyl-1-thio-α-L-arabinopyranoside 12 with 87% and 59% yields respectively. Donor 13 was reacted with xylose acceptor 11 to afford the Ara-α-(1→4)-Xyl disaccharide 17. Thiolglycoside donor 16 coupled with xylose acceptor 6 to afford the Ara-α-(1→2)-Xyl disaccharide 19. Glycosylation of disaccharide donor 17 with acceptor 19 gave tetrasaccharide fragment under the action of NIS and TMSOTf. Results Ara-α-(1→4)-Xyl-β-(1→3)-[Ara-α-(1→2)]-Xyl tetrasaccharide fragment 20 was obtained in 83% yields by [2+2] convergent strategy, providing the material basis and technology for the synthesis of the marine glycolipid Erylusamine B. |
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