[(2S,3R,4R,5S,6R)-4,5-dibenzoyloxy-2-methyl-6-(2,2,2-trichloroethanimidoyl)oxyoxan-3-yl] benzoate | 400605-72-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2S,3R,4R,5S,6R)-4,5-dibenzoyloxy-2-methyl-6-(2,2,2-trichloroethanimidoyl)oxyoxan-3-yl] benzoate
• CAS: 400605-72-3
• 化学式: C₂₉H₂₄Cl₃NO₈
• 分子量: 620.87
• InChiKey: PXEXKKMRQLSGBP-AAWVMLDPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.77
• 重原子数：
  41.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  121.21
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  [(2S,3R,4R,5S,6R)-4,5-dibenzoyloxy-2-methyl-6-(2,2,2-trichloroethanimidoyl)oxyoxan-3-yl] benzoate 在 sodium methylate 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 8.5h， 生成 hexanoate oleanate 3-O-α-L-fucopyranoside
  参考文献：
  名称：

  Synthesis and biological evaluation of oleanolic acid derivatives as PTP1B inhibitors

  摘要：

  Twenty-four sugar-substituted oleanolic acid derivatives (1a-1f, 2a-2j, and 3a-3h) were synthesized in a concise and efficient strategy and their effects on the inhibition of protein tyrosine phosphatase 1B (PTP1B) and insulin-sensitizing response were evaluated in vitro. Several derivatives showed moderate to good inhibitory activities against PTP1B, and especially compounds 2f, 2h, 3d and 3e exhibited the most potent inhibitory activities with the IC50 values of 1.91, 12.2, 9.21 and 0.56 mu M against PTP1B, respectively. Furthermore, compounds 2g-2h and 3b-3e displayed good insulin-sensitizing activities with the response values ranging from 21.52% to 59.58%. Structure-activity relationship study of these sugar-substituted oleanolic acid derivatives demonstrated that PTP1B inhibitory activity and insulin-sensitizing response were strongly influenced by both the carbohydrate moiety at the C-3 position and the long acidic chain at C-28 position of oleanolic acid. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.03.001

文献信息

• Regioselective single pot C3-glycosylation of strophanthidol using methylboronic acid as a transient protecting group
  作者：Jia-Hui Tay、Valentin Dorokhov、Sibin Wang、Pavel Nagorny

  DOI：10.1038/s41429-019-0172-1

  日期：2019.6

  a single pot protocol for the selective introduction of unprotected sugars to the C3 position of the cardiotonic steroid strophanthidol. These reactions proceed with high levels of regiocontrol (>20:1 rr) in the presence of three other hydroxyl functionalities including the C19 primary hydroxyl group and could be applied to different sugars to provide the deprotected cardiac glycosides upon work up

  该手稿描述了一个单罐协议，用于将未保护的糖选择性引入到强心类固醇抗精神病药C3的C3位置。这些反应在存在其他三个羟基官能团（包括C19伯羟基）的情况下，以高水平的区域控制（> 20：1 rr）进行，可以应用于不同的糖类，以在后处理时提供去保护的强心苷（5例，77）每次操作的收益为-69％）。反应性较低的C3位置的选择性糖基化反应是通过使用甲基硼酸进行无痕保护来实现的，该保护基通过形成环状硼酸酯来封闭C5和C19羟基，然后进行原位糖基化并用甲醇中的氨进行后处理以除去硼酸酯和碳水化合物酯的保护基。