(2S,3S)-3-hydroxy-2-(hydroxymethyl)decanoic acid | 214260-90-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: (2S,3S)-3-hydroxy-2-(hydroxymethyl)decanoic acid
• CAS: 214260-90-9
• 化学式: C₁₁H₂₂O₄
• 分子量: 218.293
• InChiKey: JTPQXSWTYRIXCN-UWVGGRQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,3S)-3-hydroxy-2-(hydroxymethyl)decanoic acid 在 苯磺酰氯 作用下， 以 吡啶 为溶剂， 反应 18.0h， 生成 (3S,4S)-4-heptyl-3-(trityloxymethyl)oxetan-2-one
  参考文献：
  名称：

  Oxazoline N-Oxide-Mediated [2 + 3] Cycloadditions: Application to a Total Synthesis of the Hypocholesterolemic Agent 1233A

  摘要：

  Oxetanone 1233A1 has been synthesized in 22 steps and 3.43% overall yield from 3-methylglutaric anhydride. Asymmetric carbon at C-7 was introduced by a diastereoselective esterification of 3-methylglutaric anhydride, whereas the two asymmetric carbons at C-2' and C-3' were controlled by an asymmetric [2 +/- 3] cycloaddition using camphor-derived oxazoline N-oxide as dipole.

  DOI：

  10.1021/jo980813u
• 作为产物：
  描述：

  反式-2-癸烯酸乙酯 在 盐酸 、 sodium chlorite 、 sodium dihydrogenphosphate 、 4 Angstroem MS 、 双氧水 、 二异丁基氢化铝 、 间氯过氧苯甲酸 、 calcium carbonate 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 24.25h， 生成 (2S,3S)-3-hydroxy-2-(hydroxymethyl)decanoic acid
  参考文献：
  名称：

  Oxazoline N-Oxide-Mediated [2 + 3] Cycloadditions: Application to a Total Synthesis of the Hypocholesterolemic Agent 1233A

  摘要：

  Oxetanone 1233A1 has been synthesized in 22 steps and 3.43% overall yield from 3-methylglutaric anhydride. Asymmetric carbon at C-7 was introduced by a diastereoselective esterification of 3-methylglutaric anhydride, whereas the two asymmetric carbons at C-2' and C-3' were controlled by an asymmetric [2 +/- 3] cycloaddition using camphor-derived oxazoline N-oxide as dipole.

  DOI：

  10.1021/jo980813u

文献信息

• Oxazoline <i>N</i>-Oxide-Mediated [2 + 3] Cycloadditions: Application to a Total Synthesis of the Hypocholesterolemic Agent 1233A
  作者：Olivier Dirat、Cyrille Kouklovsky、Yves Langlois

  DOI：10.1021/jo980813u

  日期：1998.9.1

  Oxetanone 1233A1 has been synthesized in 22 steps and 3.43% overall yield from 3-methylglutaric anhydride. Asymmetric carbon at C-7 was introduced by a diastereoselective esterification of 3-methylglutaric anhydride, whereas the two asymmetric carbons at C-2' and C-3' were controlled by an asymmetric [2 +/- 3] cycloaddition using camphor-derived oxazoline N-oxide as dipole.