(1S,2S)-1-[4-methoxy-3-(methoxymethoxy)phenyl]-2-(3,4,5-trimethoxyphenyl)ethane-1,2-diol | 213313-13-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (1S,2S)-1-[4-methoxy-3-(methoxymethoxy)phenyl]-2-(3,4,5-trimethoxyphenyl)ethane-1,2-diol
• CAS: 213313-13-4
• 化学式: C₂₀H₂₆O₈
• 分子量: 394.422
• InChiKey: BBUXXZKUNYYPMX-OALUTQOASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.47
• 重原子数：
  28.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  95.84
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (1S,2S)-1-[4-methoxy-3-(methoxymethoxy)phenyl]-2-(3,4,5-trimethoxyphenyl)ethane-1,2-diol 在 sodium hydroxide 、 十六烷基三甲基溴化铵 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 生成 2-methoxy-5-[(4S,5S)-5-(3,4,5-trimethoxyphenyl)-1,3-dioxolan-4-yl]phenol
  参考文献：
  名称：

  Asymmetric synthesis of antimitotic combretadioxolane with potent antitumor activity against multi-drug resistant cells

  摘要：

  The (S,S)-enantiomer of combretadioxolane (3), designed as a chirally preorganized derivative of combretastatin A-4, exhibited quite strong tubulin polymerization-inhibitory activity (IC50: 4-6 mu M) (S,S)-3 is 20 times more potent than vincristine as an in vitro growth inhibitor (in terms of GI(50)) of the multi-drug-resistant (MDR) cell line PC-12, which produces P-glycoprotein. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00344-8
• 作为产物：
  描述：

  [(3,4,5-trimethoxyphenyl)methyl]phosphoric acid diethyl ester 在 AD-mix-α 、 甲基磺酰胺 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 叔丁醇 为溶剂， 生成 (1S,2S)-1-[4-methoxy-3-(methoxymethoxy)phenyl]-2-(3,4,5-trimethoxyphenyl)ethane-1,2-diol
  参考文献：
  名称：

  Asymmetric synthesis of antimitotic combretadioxolane with potent antitumor activity against multi-drug resistant cells

  摘要：

  The (S,S)-enantiomer of combretadioxolane (3), designed as a chirally preorganized derivative of combretastatin A-4, exhibited quite strong tubulin polymerization-inhibitory activity (IC50: 4-6 mu M) (S,S)-3 is 20 times more potent than vincristine as an in vitro growth inhibitor (in terms of GI(50)) of the multi-drug-resistant (MDR) cell line PC-12, which produces P-glycoprotein. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00344-8

文献信息

• Asymmetric synthesis of antimitotic combretadioxolane with potent antitumor activity against multi-drug resistant cells
  作者：Ryuichi Shirai、Hisae Takayama、Asuka Nishikawa、Yukiko Koiso、Yuichi Hashimoto

  DOI：10.1016/s0960-894x(98)00344-8

  日期：1998.8

  The (S,S)-enantiomer of combretadioxolane (3), designed as a chirally preorganized derivative of combretastatin A-4, exhibited quite strong tubulin polymerization-inhibitory activity (IC50: 4-6 mu M) (S,S)-3 is 20 times more potent than vincristine as an in vitro growth inhibitor (in terms of GI(50)) of the multi-drug-resistant (MDR) cell line PC-12, which produces P-glycoprotein. (C) 1998 Elsevier Science Ltd. All rights reserved.