Synthesis of a Trisaccharide Related to the Cytotoxic Triterpenoid Saponins Isolated from the Bark of Albizia procera

被引：2

作者：

Liu, Qing-Chao ^{[1
]}

Guo, Tian-Tian ^{[2
]}

Zhao, Cong ^{[1
]}

Sun, Jing ^{[1
]}

Li, Wen-Hong ^{[1
]}

机构：

[1] NW Univ Xian, Dept Pharmaceut Engn, Xian 710069, Peoples R China

[2] Xian Inst Food & Drug Control, Dept Med Chem, Xian 710054, Peoples R China

来源：

HELVETICA CHIMICA ACTA | 2014年 / 97卷 / 03期

基金：

中国博士后科学基金;

关键词：

Glycosylation; Aglycone; 4-methoxyphenyl-; Triterpenoid saponins; Saponins; Glucosamine; N-acetyl-; INTERMOLECULAR H-BONDS; INHIBITORY-ACTIVITY; ANTITUMOR-ACTIVITY; H-1-NMR ANALYSIS; HYDROXY-GROUPS; RAIN-FOREST; GLYCOSIDES; ALCOHOLS; DMSO; ACID;

D O I：

10.1002/hlca.201300195

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Chemical synthesis of a trisaccharide related to the cytotoxic triterpenoid saponins isolated from the bark of Albizia procera has been accomplished through a concise stepwise glycosylation strategy starting from commercially available D-xylose, 2-acetamido-2-deoxy-D-glucose and L-arabinose. The target trisaccharide was designed with a 4-methoxyphenyl (MP) aglycone to extend the scope of conversion to suitable glycoconjugates via selective removal of 4-methoxyphenyl (MP) group. An unexpected phenomenon, i.e., the arabinosyl residue assumed the C-1(4) conformation instead of the typical C-4(1) form, was observed. Deprotection could restore the normal conformation.

引用

页码：361 / 368

页数：8

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