(3S,4S,5R)-4-(benzyloxy)-5-((R)-1-iodotetradecyl) tetrahydrofuran-3-ylcarbamate | 1453202-89-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3S,4S,5R)-4-(benzyloxy)-5-((R)-1-iodotetradecyl) tetrahydrofuran-3-ylcarbamate
• 英文别名: tert-butyl N-[(3S,4S,5R)-5-[(1R)-1-iodotetradecyl]-4-phenylmethoxyoxolan-3-yl]carbamate
• CAS: 1453202-89-5
• 化学式: C₃₀H₅₀INO₄
• 分子量: 615.636
• InChiKey: CESSWIQIZZPCFR-UNFRKHOWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10
• 重原子数：
  36
• 可旋转键数：
  19
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  56.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3S,4S,5R)-4-(benzyloxy)-5-((R)-1-iodotetradecyl) tetrahydrofuran-3-ylcarbamate 在 三正丁基氢锡 、 1,1'-偶氮(氰基环己烷) 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 3.0h， 生成 jaspine B*TFA
  参考文献：
  名称：

  Stereoselective total synthesis of Jaspine B (Pachastrissamine) utilizing iodocyclization and an investigation of its cytotoxic activity

  摘要：

  The stereoselective synthesis of Jaspine B has been achieved from easily available (S)-Garner's aldehyde. The trisubstituted tetrahydrofuran core of Jaspine B was constructed by utilizing a diastereoselective iodocyclization as the key step. Deiodination and debenzylation were performed in a single step by using n-Bu3SnH and ABCN as a conjugate catalyst system. The in vitro cytotoxicity of compounds 1 and la against 3 human cancer cell lines-A549 (lung), MCF7 (breast), and KB (oral): and a non-cancer cell line (NIH3T3) was determined by sulphorhodamine B based assay. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.07.003
• 作为产物：
  描述：

  (S)-tert-butyl 4-((R)-1-(benzyloxy)hexadec-2-enyl)-2, 2-dimethyloxazolidine-3-carboxylate 在 N-碘代丁二酰亚胺 、 碘 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 2.5h， 生成 (3S,4S,5R)-4-(benzyloxy)-5-((R)-1-iodotetradecyl) tetrahydrofuran-3-ylcarbamate
  参考文献：
  名称：

  Stereoselective total synthesis of Jaspine B (Pachastrissamine) utilizing iodocyclization and an investigation of its cytotoxic activity

  摘要：

  The stereoselective synthesis of Jaspine B has been achieved from easily available (S)-Garner's aldehyde. The trisubstituted tetrahydrofuran core of Jaspine B was constructed by utilizing a diastereoselective iodocyclization as the key step. Deiodination and debenzylation were performed in a single step by using n-Bu3SnH and ABCN as a conjugate catalyst system. The in vitro cytotoxicity of compounds 1 and la against 3 human cancer cell lines-A549 (lung), MCF7 (breast), and KB (oral): and a non-cancer cell line (NIH3T3) was determined by sulphorhodamine B based assay. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.07.003