[(2S)-2-hydroxy-3-[(1S,3S,6S,9S,12S,14R,16R,18S,20R,21R,22S,26R,29S,31R,32S,33R,35R,36S)-21-methoxy-14-methyl-8,15-dimethylidene-24-oxo-2,19,30,34,37,39,40,41-octaoxanonacyclo[24.9.2.13,32.13,33.16,9.112,16.018,22.029,36.031,35]hentetracontan-20-yl]propyl] methanesulfonate | 253128-19-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃吡喃类
• 英文名称: [(2S)-2-hydroxy-3-[(1S,3S,6S,9S,12S,14R,16R,18S,20R,21R,22S,26R,29S,31R,32S,33R,35R,36S)-21-methoxy-14-methyl-8,15-dimethylidene-24-oxo-2,19,30,34,37,39,40,41-octaoxanonacyclo[24.9.2.13,32.13,33.16,9.112,16.018,22.029,36.031,35]hentetracontan-20-yl]propyl] methanesulfonate
• CAS: 253128-19-7
• 化学式: C₄₁H₆₀O₁₄S
• 分子量: 808.985
• InChiKey: VQTYKLFDXJKMAI-GMJBIAOCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  56
• 可旋转键数：
  6
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  172
• 氢给体数：
  1
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  [(2S)-2-hydroxy-3-[(1S,3S,6S,9S,12S,14R,16R,18S,20R,21R,22S,26R,29S,31R,32S,33R,35R,36S)-21-methoxy-14-methyl-8,15-dimethylidene-24-oxo-2,19,30,34,37,39,40,41-octaoxanonacyclo[24.9.2.13,32.13,33.16,9.112,16.018,22.029,36.031,35]hentetracontan-20-yl]propyl] methanesulfonate 在 水 、 叠氮化四丁基铵 、 三甲基膦 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.5h， 生成 艾瑞布林
  参考文献：
  名称：

  METHODS USEFUL IN THE SYNTHESIS OF HALICHONDRIN B ANALOGS

  摘要：

  总的来说，本发明涉及改进的方法，用于合成半龙脂素B的类似物，如厄立宾及其药用盐（例如，厄立宾甲磺酸盐）。

  公开号：

  US20150158881A1
• 作为产物：
  描述：

  甲基磺酰氯 、 艾瑞布林中间体 在 2,4,6-三甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 76.67h， 以95%的产率得到[(2S)-2-hydroxy-3-[(1S,3S,6S,9S,12S,14R,16R,18S,20R,21R,22S,26R,29S,31R,32S,33R,35R,36S)-21-methoxy-14-methyl-8,15-dimethylidene-24-oxo-2,19,30,34,37,39,40,41-octaoxanonacyclo[24.9.2.13,32.13,33.16,9.112,16.018,22.029,36.031,35]hentetracontan-20-yl]propyl] methanesulfonate
  参考文献：
  名称：

  METHODS USEFUL IN THE SYNTHESIS OF HALICHONDRIN B ANALOGS

  摘要：

  总的来说，本发明涉及改进的方法，用于合成半龙脂素B的类似物，如厄立宾及其药用盐（例如，厄立宾甲磺酸盐）。

  公开号：

  US20150158881A1

文献信息

• Intermediate compounds for preparing macrocylcic analogs
  申请人：Eisai Co., Ltd.

  公开号：US06365759B1

  公开（公告）日：2002-04-02

  Intermediate compounds of the formulas for use in the preparation of macrocyclic analogs.

  用于制备大环类似物的中间化合物的化学式。
• METHODS USEFUL IN THE SYNTHESIS OF HALICHONDRIN B ANALOGS
  申请人：Eisai R&D Management Co., Ltd.

  公开号：US20150158881A1

  公开（公告）日：2015-06-11

  In general, the present invention features improved methods useful for the synthesis of analogs of halichondrin B, such as eribulin and pharmaceutically acceptable salts thereof (e.g., eribulin mesylate).

  总的来说，本发明涉及改进的方法，用于合成半龙脂素B的类似物，如厄立宾及其药用盐（例如，厄立宾甲磺酸盐）。
• Effective procedure for selective ammonolysis of monosubstituted oxiranes: application to E7389 synthesis
  作者：Yosuke Kaburagi、Yoshito Kishi

  DOI：10.1016/j.tetlet.2007.10.116

  日期：2007.12

  A highly effective procedure is reported to synthesize 1,2-aminoalcohols by regio- and chemo-selective ammonolysis of mono-substituted epoxides. Additive- and concentration-effects were studied, revealing that (1) methanesulfonic acid is most effective among the additives tested and (2) formation of bis-adducts is practically eliminated at [C] <= 40 mM. The optimum condition thus identified was successfully applied to the final step of the synthesis of potent anti-tumor compound E7389. (c) 2007 Elsevier Ltd. All rights reserved.
• Macrocyclic ketone analogues of halichondrin B
  作者：Wanjun Zheng、Boris M. Seletsky、Monica H. Palme、Paul J. Lydon、Lori A. Singer、Charles E. Chase、Charles A. Lemelin、Yongchun Shen、Heather Davis、Lynda Tremblay、Murray J. Towle、Kathleen A. Salvato、Bruce F. Wels、Kimberley K. Aalfs、Yoshito Kishi、Bruce A. Littlefield、Melvin J. Yu

  DOI：10.1016/j.bmcl.2004.08.069

  日期：2004.11

  Structurally simplified macrocyclic ketone analogues of halichondrin B were prepared by total synthesis and found to retain the potent cell growth inhibitory activity in vitro, stability in mouse serum, and in vivo efficacy of the natural product. (C) 2004 Elsevier Ltd. All rights reserved.