(E)-(3S,4R)-3-Methoxymethoxy-4-methyl-6-phenyl-hex-5-en-1-ol | 352281-78-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (E)-(3S,4R)-3-Methoxymethoxy-4-methyl-6-phenyl-hex-5-en-1-ol
• 英文别名: (E,3S,4R)-3-(methoxymethoxy)-4-methyl-6-phenylhex-5-en-1-ol
• CAS: 352281-78-8
• 化学式: C₁₅H₂₂O₃
• 分子量: 250.338
• InChiKey: GBXJEIIIFKSQMV-HOMMJUPQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-(3S,4R)-3-Methoxymethoxy-4-methyl-6-phenyl-hex-5-en-1-ol 在 2,4,6-三氯苯甲酰氯 、 4-甲基苯磺酸吡啶 、 sodium hydride 、 戴斯-马丁氧化剂 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 叔丁醇 为溶剂， 反应 12.33h， 生成 [(1E,3R,4S,6E)-8-[[(2R)-3-(4-methoxyphenyl)-1-oxo-1-(2-trimethylsilylethoxy)propan-2-yl]amino]-3-methyl-8-oxo-1-phenylocta-1,6-dien-4-yl] (2R)-6-[(2-methylpropan-2-yl)oxycarbonylamino]-2-(2-methylpropyl)-4-oxohexanoate
  参考文献：
  名称：

  Synthesis of stable analogs in blood and conformational analysis of arenastatin A, a potent cytotoxic spongean depsipeptide

  摘要：

  In order to produce stable analogs in blood of arenastatin A, a potent cytotoxic depsipeptide from the marine sponge Dysidea arenaria, we synthesized four analogs in which the 15-20 ester linkage was modified. Among them, the carba analog and 20-deoxo analog showed stability in serum. The conformation of arenastatin A and its three analogs were analyzed by distance-restrained molecular dynamic calculation to elucidate a three-dimensional stereostructure contributing to the extremely potent cytotoxicity of arenastatin A. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00339-8
• 作为产物：
  描述：

  (E)-(3S,4R)-1-(tert-Butyl-diphenyl-silanyloxy)-4-methyl-6-phenyl-hex-5-en-3-ol 在 四丁基氟化铵 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 13.0h， 生成 (E)-(3S,4R)-3-Methoxymethoxy-4-methyl-6-phenyl-hex-5-en-1-ol
  参考文献：
  名称：

  Synthesis of stable analogs in blood and conformational analysis of arenastatin A, a potent cytotoxic spongean depsipeptide

  摘要：

  In order to produce stable analogs in blood of arenastatin A, a potent cytotoxic depsipeptide from the marine sponge Dysidea arenaria, we synthesized four analogs in which the 15-20 ester linkage was modified. Among them, the carba analog and 20-deoxo analog showed stability in serum. The conformation of arenastatin A and its three analogs were analyzed by distance-restrained molecular dynamic calculation to elucidate a three-dimensional stereostructure contributing to the extremely potent cytotoxicity of arenastatin A. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00339-8

文献信息

• Synthesis of stable analogs in blood and conformational analysis of arenastatin A, a potent cytotoxic spongean depsipeptide
  作者：Nobutoshi Murakami、Satoru Tamura、Weiqi Wang、Tatsuya Takagi、Motomasa Kobayashi

  DOI：10.1016/s0040-4020(01)00339-8

  日期：2001.5

  In order to produce stable analogs in blood of arenastatin A, a potent cytotoxic depsipeptide from the marine sponge Dysidea arenaria, we synthesized four analogs in which the 15-20 ester linkage was modified. Among them, the carba analog and 20-deoxo analog showed stability in serum. The conformation of arenastatin A and its three analogs were analyzed by distance-restrained molecular dynamic calculation to elucidate a three-dimensional stereostructure contributing to the extremely potent cytotoxicity of arenastatin A. (C) 2001 Elsevier Science Ltd. All rights reserved.