Acetic acid (1S,2R,3S,4R)-4-acetoxy-2-benzyloxymethyl-3-cyanomethyl-cyclopentyl ester | 53398-47-3

• 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: Acetic acid (1S,2R,3S,4R)-4-acetoxy-2-benzyloxymethyl-3-cyanomethyl-cyclopentyl ester
• CAS: 53398-47-3
• 化学式: C₁₉H₂₃NO₅
• 分子量: 345.395
• InChiKey: KYGDXLNJULQCOH-OKYOBFRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.62
• 重原子数：
  25.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  85.62
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  ((1R,2R,3S,4S)-3-Hydroxymethyl-5,6-dimethyl-bicyclo[2.2.1]hept-5-en-2-yl)-acetonitrile 生成 Acetic acid (1S,2R,3S,4R)-4-acetoxy-2-benzyloxymethyl-3-cyanomethyl-cyclopentyl ester
  参考文献：
  名称：

  天然和非天然前列腺素的手性经济全合成

  摘要：

  AbstractUsing a meso‐compound which is asymmetrically substituted with a chiral moiety as an intermediate, prostaglandins have been synthesized. Since the undesired enantiomer is readily recycled, this approach leads to a synthesis with high chiral efficiency. In addition it is possible to prepare both enantiomeric configurations of prostaglandins by simply altering the sequence of reactions. This concept should be generally useful in the synthesis of optically active molecules.

  DOI：

  10.1002/hlca.19750580228