Methyl <4(R)-<1α,4β,4(Z)>>-4-hydroxy-4-<1-<(2-methoxy-2-oxoethyl)thio>-2-hexadecenyl>cyclohexanecarboxylate | 132410-28-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Methyl <4(R)-<1α,4β,4(Z)>>-4-hydroxy-4-<1-<(2-methoxy-2-oxoethyl)thio>-2-hexadecenyl>cyclohexanecarboxylate
• 英文别名: Methyl <4(R)-<1β,4β,4(Z)>>-4-hydroxy-4-<1-<(2-methoxy-2-oxoethyl)thio>-2-hexadecenyl>cyclohexanecarboxylate；Methyl [4(R)-(1α,4β,4(Z))]-4-hydroxy-4-{1-[(2-methoxy-2-oxoethyl)thio]-2-hexadecenyl}cyclohexanecarboxylate
• CAS: 132410-28-7
• 化学式: C₂₇H₄₈O₅S
• 分子量: 484.741
• InChiKey: XCLIDOMFVHCLRO-HEUGVGRNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.61
• 重原子数：
  33.0
• 可旋转键数：
  18.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  72.83
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  Methyl <4(R)-<1α,4β,4(Z)>>-4-hydroxy-4-<1-<(2-methoxy-2-oxoethyl)thio>-2-hexadecenyl>cyclohexanecarboxylate 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 以60%的产率得到<4(R)-<1α,4β,4(Z)>>-4-<1-<(Carboxymethyl)thio>-2-hexadecenyl>-4-hydroxycyclohexanecarboxylic acid
  参考文献：
  名称：

  Conformationally restricted leukotriene antagonists. Synthesis of chiral 4-hydroxy-4-alkylcyclohexanecarboxylic acids as leukotriene D4 analogs

  摘要：

  Eight conformationally restricted LTD4 analogues, 2a-d (n = 1, 2), were prepared in nine steps from methyl 4-hydroxybenzoate (3). The key step in this approach is the Sharpless asymmetric epoxidation of allylic alcohol 8 in which all four possible epoxy alcohol diastereomers 9a-d were prepared. A single-crystal X-ray analysis of 9b and application of the Sharpless model for predicting epoxidation stereoselectivity led to the assignment of relative stereochemistry and absolute configuration of 9a-d. These high optical purity epoxy alcohols were then converted to chiral LTD4 analogues 2a-d (n = 1, 2) in three steps.

  DOI：

  10.1021/jo00005a019
• 作为产物：
  描述：

  正十四烷基三苯基溴化膦 在 potassium tert-butylate 、 三乙胺 作用下， 以 甲醇 为溶剂， 反应 24.08h， 生成 Methyl <4(R)-<1α,4β,4(Z)>>-4-hydroxy-4-<1-<(2-methoxy-2-oxoethyl)thio>-2-hexadecenyl>cyclohexanecarboxylate
  参考文献：
  名称：

  Conformationally restricted leukotriene antagonists. Synthesis of chiral 4-hydroxy-4-alkylcyclohexanecarboxylic acids as leukotriene D4 analogs

  摘要：

  Eight conformationally restricted LTD4 analogues, 2a-d (n = 1, 2), were prepared in nine steps from methyl 4-hydroxybenzoate (3). The key step in this approach is the Sharpless asymmetric epoxidation of allylic alcohol 8 in which all four possible epoxy alcohol diastereomers 9a-d were prepared. A single-crystal X-ray analysis of 9b and application of the Sharpless model for predicting epoxidation stereoselectivity led to the assignment of relative stereochemistry and absolute configuration of 9a-d. These high optical purity epoxy alcohols were then converted to chiral LTD4 analogues 2a-d (n = 1, 2) in three steps.

  DOI：

  10.1021/jo00005a019