8-((3S,4S)-4-Carboxy-3-hydroxy-5-trityloxy-pentyl)-naphthalene-2-carboxylic acid methyl ester | 188053-25-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 8-((3S,4S)-4-Carboxy-3-hydroxy-5-trityloxy-pentyl)-naphthalene-2-carboxylic acid methyl ester
• 英文别名: (2S,3S)-3-hydroxy-5-(7-methoxycarbonylnaphthalen-1-yl)-2-(trityloxymethyl)pentanoic acid
• CAS: 188053-25-0
• 化学式: C₃₇H₃₄O₆
• 分子量: 574.673
• InChiKey: ZUFSPHWQZXOTEA-HEVIKAOCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  43
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  93.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  8-((3S,4S)-4-Carboxy-3-hydroxy-5-trityloxy-pentyl)-naphthalene-2-carboxylic acid methyl ester 在 对甲苯磺酰氯 作用下， 以 吡啶 为溶剂， 以96%的产率得到trans-4-<2-(7-methoxycarbonyl-1-naphthyl)ethyl>-3-triphenylmethoxymethyl-2-oxetanone
  参考文献：
  名称：

  Synthesis of Four Chiral Isomers of β-Lactone DU-6622 and Inhibition of HMG-CoA Synthase by the Specific (2R,3R)-Isomer

  摘要：

  Four chiral forms of the beta-lactone DU-6622 (3-hydroxy-2-(hydroxymethyl)-5-[7-(methoxycarbonyl)-naphthalen-1-yl]pentanoic acid 1,3-lactone) were prepared to investigate their inhibitory activity against 3-hydroxy-3-methylglutarly-CoA (HMG-CoA) synthase. The (2R,3R)-beta-lactone isomer (+)-8a, having the same stereochemistry as that of the fungal beta-lactone 1233A, showed the most potent HMG-CoA synthase inhibitory activity(IC50: 0.098 mu M). The other three beta-lactone isomers, (2S,3R)- ((-)-8b), (2S,3S)- ((-)-8a), and (2R,3S)-isomers ((+)-8b), were weaker inhibitors with larger IC50 values of 9.4, 31, and 360 mu M, respectively. Thus, it was concluded that the (2R,3R) stereochemistry of the beta-lactone ring is responsible for HMG-CoA synthase inhibition.

  DOI：

  10.1021/jo9621433
• 作为产物：
  描述：

  8-[(3S,4S)-4-Carboxy-3-((S)-2-methoxy-2-phenyl-acetoxy)-5-trityloxy-pentyl]-naphthalene-2-carboxylic acid methyl ester 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以90%的产率得到8-((3S,4S)-4-Carboxy-3-hydroxy-5-trityloxy-pentyl)-naphthalene-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis of Four Chiral Isomers of β-Lactone DU-6622 and Inhibition of HMG-CoA Synthase by the Specific (2R,3R)-Isomer

  摘要：

  Four chiral forms of the beta-lactone DU-6622 (3-hydroxy-2-(hydroxymethyl)-5-[7-(methoxycarbonyl)-naphthalen-1-yl]pentanoic acid 1,3-lactone) were prepared to investigate their inhibitory activity against 3-hydroxy-3-methylglutarly-CoA (HMG-CoA) synthase. The (2R,3R)-beta-lactone isomer (+)-8a, having the same stereochemistry as that of the fungal beta-lactone 1233A, showed the most potent HMG-CoA synthase inhibitory activity(IC50: 0.098 mu M). The other three beta-lactone isomers, (2S,3R)- ((-)-8b), (2S,3S)- ((-)-8a), and (2R,3S)-isomers ((+)-8b), were weaker inhibitors with larger IC50 values of 9.4, 31, and 360 mu M, respectively. Thus, it was concluded that the (2R,3R) stereochemistry of the beta-lactone ring is responsible for HMG-CoA synthase inhibition.

  DOI：

  10.1021/jo9621433