(2Z,2'R,2''E,3'R,4S,5'S,6'S)-N-{6'-[4''-(1''',3'''-benzothiazol-2'''-ylsulfonyl)-3''-methylbut-2''-en-1''-yl]-2',5'-dimethyltetrahydropyran-3'-yl}-4-t-butyldimethylsilyloxypent-2-enamide | 878673-39-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: (2Z,2'R,2''E,3'R,4S,5'S,6'S)-N-{6'-[4''-(1''',3'''-benzothiazol-2'''-ylsulfonyl)-3''-methylbut-2''-en-1''-yl]-2',5'-dimethyltetrahydropyran-3'-yl}-4-t-butyldimethylsilyloxypent-2-enamide
• 英文别名: (Z,4S)-N-[(2R,3R,5S,6S)-6-[(E)-4-(1,3-benzothiazol-2-ylsulfonyl)-3-methylbut-2-enyl]-2,5-dimethyloxan-3-yl]-4-[tert-butyl(dimethyl)silyl]oxypent-2-enamide
• CAS: 878673-39-3
• 化学式: C₃₀H₄₆N₂O₅S₂Si
• 分子量: 606.923
• InChiKey: FJQUBHKEOLGZDD-WPGNWSFPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.67
• 重原子数：
  40
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  131
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2Z,2'R,2''E,3'R,4S,5'S,6'S)-N-{6'-[4''-(1''',3'''-benzothiazol-2'''-ylsulfonyl)-3''-methylbut-2''-en-1''-yl]-2',5'-dimethyltetrahydropyran-3'-yl}-4-t-butyldimethylsilyloxypent-2-enamide 在 盐酸 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 为溶剂， 反应 13.0h， 生成 (Z)-(S)-4-Hydroxy-pent-2-enoic acid ((2R,3R,5S,6S)-6-{(2E,4E)-5-[(3R,4R,5R,7S)-4-(tert-butyl-dimethyl-silanyloxy)-7-methoxy-7-methyl-1,6-dioxa-spiro[2.5]oct-5-yl]-3-methyl-penta-2,4-dienyl}-2,5-dimethyl-tetrahydro-pyran-3-yl)-amide
  参考文献：
  名称：

  Total synthesis of FR901464: second generation

  摘要：

  FR901464, a potent cell cycle inhibitor, was synthesized in a convergent manner using natural chiral Pool, L-threonine, ethyl (S)-lactate and 2-deoxy-D-glucose as starting materials. (c) 2005 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2005.11.031
• 作为产物：
  描述：

  (S,Z)-methyl 4-((tert-butyldimethylsilyl)oxy)pent-2-enoate 在 N-乙基吗啉 、 lithium hydroxide 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 作用下， 以 甲醇 、 水 、 乙腈 为溶剂， 反应 18.0h， 生成 (2Z,2'R,2''E,3'R,4S,5'S,6'S)-N-{6'-[4''-(1''',3'''-benzothiazol-2'''-ylsulfonyl)-3''-methylbut-2''-en-1''-yl]-2',5'-dimethyltetrahydropyran-3'-yl}-4-t-butyldimethylsilyloxypent-2-enamide
  参考文献：
  名称：

  Total synthesis of FR901464: second generation

  摘要：

  FR901464, a potent cell cycle inhibitor, was synthesized in a convergent manner using natural chiral Pool, L-threonine, ethyl (S)-lactate and 2-deoxy-D-glucose as starting materials. (c) 2005 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2005.11.031

文献信息

• Design and synthesis of a phenyl C-glycoside derivative of Spliceostatin A and its biological evaluation toward prostate cancer treatment
  作者：Yusuke Yoshikawa、Airi Ishibashi、Kenichi Murai、Yasufumi Kaneda、Keisuke Nimura、Mitsuhiro Arisawa

  DOI：10.1016/j.tetlet.2019.151313

  日期：2019.12

  synthesized a novel phenyl C-glycoside analogue of Spliceostatin A, which is potent splicing inhibitor and has anti-cancer activities. We successfully synthesized its right phenyl C-glycoside sugar fragment in shorter steps compared to previous synthetic methods for Spliceostatin A and revealed an appropriate fragment combination with a Julia-coupling reaction. Regarding biological activity, the Ph-C-glycoside

  我们设计并合成了新型的Spliceostatin A苯基C-糖苷类似物，它是有效的剪接抑制剂，具有抗癌活性。与以前的Spliceostatin A合成方法相比，我们以较短的步骤成功合成了其正确的苯基C-糖苷糖片段，并揭示了具有朱莉娅偶联反应的适当片段组合。关于生物学活性，Spliceostatin A的Ph- C-糖苷类似物在三种前列腺癌细胞系中显示出抑制的细胞增殖，并抑制了AR-V7表达。