ursolic acid trityl ester | 947730-20-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: ursolic acid trityl ester
• 英文别名: trityl ursolic ester
• CAS: 947730-20-3
• 化学式: C₄₉H₆₂O₃
• 分子量: 699.029
• InChiKey: OCEWBHPFKVUZAW-QPZTYDFESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.54
• 重原子数：
  52.0
• 可旋转键数：
  5.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  ursolic acid trityl ester 在 三氟甲磺酸三甲基硅酯 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 3-O-α-L-arabinopyranosyl ursolic acid
  参考文献：
  名称：

  Synthesis of two bidesmosidic ursolic acid saponins bearing a 2,3-branched trisaccharide residue

  摘要：

  The focus of this work was on the synthesis of two bidesmosidic ursolic acid saponins bearing a 2,3-branched trisaccharide residue. Therefore, 3-O-{[beta-D-glucopyranosyl-(1-->2)]-[alpha-L-arabinopyranosyl-(1-->3)]-alpha-L-arabinopyranosyl}ursolic acid-28-O-[beta-D-glucopyranosyl] ester 1 was concisely synthesized by two strategies in 22% and 41% overall yield, respectively, and another congener 3-O-{[beta-D-xylopyranosyl-(1-->2)]-[beta-D-glucopyranosyl-(1-->3)]-alpha-L-arabinopyranosyl}ursolic acid-28-O-[beta-D-glucopyranosyl] ester 2 was also efficiently prepared in 81% overall yield. The H-1 NMR and C-13 NMR signals of saponin 2 are all consistent with those reported for the natural product. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2005.06.024
• 作为产物：
  描述：

  熊果酸 、 三苯基氯甲烷 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以82%的产率得到ursolic acid trityl ester
  参考文献：
  名称：

  Synthesis of two bidesmosidic ursolic acid saponins bearing a 2,3-branched trisaccharide residue

  摘要：

  The focus of this work was on the synthesis of two bidesmosidic ursolic acid saponins bearing a 2,3-branched trisaccharide residue. Therefore, 3-O-{[beta-D-glucopyranosyl-(1-->2)]-[alpha-L-arabinopyranosyl-(1-->3)]-alpha-L-arabinopyranosyl}ursolic acid-28-O-[beta-D-glucopyranosyl] ester 1 was concisely synthesized by two strategies in 22% and 41% overall yield, respectively, and another congener 3-O-{[beta-D-xylopyranosyl-(1-->2)]-[beta-D-glucopyranosyl-(1-->3)]-alpha-L-arabinopyranosyl}ursolic acid-28-O-[beta-D-glucopyranosyl] ester 2 was also efficiently prepared in 81% overall yield. The H-1 NMR and C-13 NMR signals of saponin 2 are all consistent with those reported for the natural product. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2005.06.024

文献信息

• Synthesis and cytotoxic activity of the N-acetylglucosamine-bearing triterpenoid saponins
  作者：Peng Wang、Jun Wang、TianTian Guo、Yingxia Li

  DOI：10.1016/j.carres.2010.01.002

  日期：2010.3

  Fourteen ursolic acid and oleanolic acid saponins with N-acetyl-beta-D-glucosamine, and (1 -> 4)-linked and (1 6)-linked N-acetyl-beta-D-glucosamine oligosaccharide residues were synthesized in a convergent manner. The structures of all compounds were confirmed by (1)H NMR and (13)C NMR spectroscopy and by mass spectrometry, and their cytotoxic activities were assayed in three cancer cell lines. Only oleanolic acid-3-yl beta-D-GluNAc showed significant cytotoxicity against HL-60 and BGC-823. (C) 2010 Published by Elsevier Ltd.