Methyl 4(R)-Hydroxy-5,6-epoxy-5(S)-methylhex-2(E)-enoate | 104840-73-5

• 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: Methyl 4(R)-Hydroxy-5,6-epoxy-5(S)-methylhex-2(E)-enoate
• 英文别名: methyl (2E,4R,5S)-5,6-epoxy-4-hydroxy-5-methylhex-2-enoate；methyl (E,4R)-4-hydroxy-4-[(2S)-2-methyloxiran-2-yl]but-2-enoate
• CAS: 104840-73-5
• 化学式: C₈H₁₂O₄
• 分子量: 172.181
• InChiKey: RMGHFJXQDIRYMI-KTSMUEJMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  59.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-乙酰-L-苯丙氨酸 、 Methyl 4(R)-Hydroxy-5,6-epoxy-5(S)-methylhex-2(E)-enoate 在 4-吡咯烷基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 生成 Methyl (4R,5S,2'R)-4-(N-Acetylphenylalanyloxy)-5,6-epoxy-5-methyl-hex-2(E)-enoate 、 Methyl (4R,5S,2'S)-4-(N-Acetylphenylalanyloxy)-5,6-epoxy-5-methyl-hex-2(E)-enoate
  参考文献：
  名称：

  Synthesis of the host-specific toxins AF-toxin IIc and AK-toxin congeners and their stereostructure-toxicity relationship.

  摘要：

  以维生素 C 为手性媒介合成了 AF 毒素 IIC 和 AK 毒素相关化合物。在这两种毒素中，三烯酸分子的两个手性中心的 C8（R）和 C9（S）构型是产生毒性作用所不可或缺的。

  DOI：

  10.1248/cpb.34.2668
• 作为产物：
  描述：

  methyl (4R,5S)-4-(tert-butyldiphenylsilyl)oxy-5,6-epoxy-5-methylhex-2-enoate 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以69%的产率得到Methyl 4(R)-Hydroxy-5,6-epoxy-5(S)-methylhex-2(E)-enoate
  参考文献：
  名称：

  Efficient stereoselective synthesis of a 1-hydroxymethyl-2-methylglycidol derivative

  摘要：

  A highly stereoselective synthesis of (2R.3S)-3,4-epoxy-3-methyl-1-(triphenylmethyl)oxybutan-2-ol 3, which is a substructure Found in some naturally-occurring bioactive compounds. was achieved starting from commercially available 3-methhyl-2-buten-1-ol 4 in three steps, using two applications of the Sharpless asymmetric epoxidation as the key stereochemistry establishing reactions. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00149-5

文献信息

• Synthesis of the host-specific toxins AF-toxin IIc and AK-toxin congeners and their stereostructure-toxicity relationship.
  作者：Hiroshi Irie、Kohei Matsumoto、Yong Zhang

  DOI：10.1248/cpb.34.2668

  日期：——

  AF-toxin IIC and AK-toxin-related compounds were synthesized from Vitamin C as a chiral meterial. In both toxins, C8 (R) and C9 (S)-configurations at the two chiral centers of the trienoic acid moiety are indispensable for the toxic effect.

  以维生素 C 为手性媒介合成了 AF 毒素 IIC 和 AK 毒素相关化合物。在这两种毒素中，三烯酸分子的两个手性中心的 C8（R）和 C9（S）构型是产生毒性作用所不可或缺的。
• Synthesis of the methyl ester of AK-toxin II, a host-specific toxin to Japanese white pear, and its congeners: Structure-toxicity relationship of the toxin.
  作者：Hiroshi IRIE、Kohei MATSUMOTO、Takao KITAGAWA、Yong ZHANG

  DOI：10.1248/cpb.38.1451

  日期：——

  Synthesis of the methyl ester of AK-toxin II, a typical host-specific toxin, toxic to Japanese white pear, and fifteen diastereoisomers as its congeners was accomplished in optically active forms starting from vitamin C as a chiral starting material. Toxicity testing of these synthetic compounds revealed that the configurations of two chiral centers in the carboxylic acid part of the toxin have an important role in the toxicity.

  以维生素 C 为手性起始材料，以光学活性形式合成了 AK 毒素 II（一种典型的宿主特异性毒素，对日本白梨有毒）的甲酯及其 15 种非对映异构体同系物。对这些合成化合物的毒性测试表明，毒素羧酸部分的两个手性中心的构型对毒性有重要影响。
• Efficient stereoselective synthesis of a 1-hydroxymethyl-2-methylglycidol derivative
  作者：Ippei Uemura、Ken Yamada、Kayo Sugiura、Hisashi Miyagawa、Tamio Ueno

  DOI：10.1016/s0957-4166(01)00149-5

  日期：2001.4

  A highly stereoselective synthesis of (2R.3S)-3,4-epoxy-3-methyl-1-(triphenylmethyl)oxybutan-2-ol 3, which is a substructure Found in some naturally-occurring bioactive compounds. was achieved starting from commercially available 3-methhyl-2-buten-1-ol 4 in three steps, using two applications of the Sharpless asymmetric epoxidation as the key stereochemistry establishing reactions. (C) 2001 Elsevier Science Ltd. All rights reserved.