Synthesis of a typical N-acetylglucosamine-containing saponin, oleanolic acid 3-yl α-L-arabinopyranosyl-(1→2)-α-L-arabinopyranosyl-(1→6)-2-acetamido-2-deoxy-β-D-glucopyranoside

Synthesis of a typical N-acetylglucosamine-containing saponin, oleanolic acid 3-yl α-L-arabinopyranosyl-(1→2)-α-L-arabinopyranosyl-(1→6)-2-acetamido-2-deoxy-β-D-glucopyranoside
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DOI:
10.1016/s0008-6215(03)00047-8
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发表时间:
2003-04-22
影响因子:
3.1
通讯作者:
Yu, B
Yu, B
中科院分区:
化学3区
文献类型:
--
作者:
Sun, JS;Han, XW;Yu, B

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从细叶金合欢和合欢中分离得到一种具有细胞毒性的皂苷,具有典型的N-乙酰氨基葡萄糖甙结构,经合成得到3-基-(1 -> 2)-α-L-阿拉伯糖甙-(1 -> 6)-2-乙酰氨基-2-脱氧-β-D-葡萄糖甙。合成采用逐步糖基化方式,使用糖基三氟乙酰亚胺酯5和9以及硫代糖苷12作为供体。(C)2003爱思唯尔科技有限公司版权所有。
Oleanolic acid 3-yl alpha-L-arabinopyranosyl-(1 --> 2)-alpha-L-arabinopyranosyl-(1 --> 6)-2-acetamido-2-deoxy-beta-D-glucopyranoside, a cytotoxic saponin isolated from Acacia tenuifolia and Albizia subdimidiata with a typical structure of the N-acetylglucosamine-containing plant saponins, was synthesized. The synthesis adopted a stepwise glycosylation fashion employing glycosyl trifluoroacetimidates 5 and 9 and thioglycoside 12 as donors. (C) 2003 Elsevier Science Ltd. All rights reserved.