(2R,4S,5S,6R,7R,8S)-2,4,6,8-Tetramethyl-dec-9-ene-1,5,7-triol | 1026797-35-2

• 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: (2R,4S,5S,6R,7R,8S)-2,4,6,8-Tetramethyl-dec-9-ene-1,5,7-triol
• 英文别名: (2R,4S,5S,6R,7R,8S)-2,4,6,8-tetramethyldec-9-ene-1,5,7-triol
• CAS: 1026797-35-2
• 化学式: C₁₄H₂₈O₃
• 分子量: 244.375
• InChiKey: MZMZVKBOHVNSPM-WFQJECDVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,4S,5S,6R,7R,8S)-2,4,6,8-Tetramethyl-dec-9-ene-1,5,7-triol 在 重铬酸吡啶 、 草酰氯 、 camphor-10-sulfonic acid 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 (3R,5S)-5-[(4S,5R,6R)-6-[(2S)-but-3-en-2-yl]-2,2,5-trimethyl-1,3-dioxan-4-yl]-1-dimethoxyphosphoryl-3-methylhexan-2-one
  参考文献：
  名称：

  An Alternative and Facile Synthesis of Pikronolide

  摘要：

  An alternative and facile synthesis of pikronolide (2), the aglycon of pikromycin (1), via coupling between the C-11-C-15 fragment (10) and the C-I-C-l0 fragment (12), Homer-Emmons cyclization, regioselective protection of the C-5-hydroxy group, and oxidation of the C-3-hydroxy group, is described. In this synthesis, the conformational analysis by NMR played mt important role.

  DOI：

  10.3987/com-97-s38
• 作为产物：
  描述：

  (3S,4R,5S)-4-hydroxy-5(2(S)-isopropyloxy-3(R),5(S)-dimethyl-6(S)-tetrahydroxypropanyl)-3-methylhexane 在 盐酸 、 calcium borohydride 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 生成 (2R,4S,5S,6R,7R,8S)-2,4,6,8-Tetramethyl-dec-9-ene-1,5,7-triol
  参考文献：
  名称：

  An Alternative and Facile Synthesis of Pikronolide

  摘要：

  An alternative and facile synthesis of pikronolide (2), the aglycon of pikromycin (1), via coupling between the C-11-C-15 fragment (10) and the C-I-C-l0 fragment (12), Homer-Emmons cyclization, regioselective protection of the C-5-hydroxy group, and oxidation of the C-3-hydroxy group, is described. In this synthesis, the conformational analysis by NMR played mt important role.

  DOI：

  10.3987/com-97-s38

文献信息

• An Alternative and Facile Synthesis of Pikronolide
  作者：Noriyuki Nakajima、MAkoto Ubukata、Osamu Yonemitsu

  DOI：10.3987/com-97-s38

  日期：——

  An alternative and facile synthesis of pikronolide (2), the aglycon of pikromycin (1), via coupling between the C-11-C-15 fragment (10) and the C-I-C-l0 fragment (12), Homer-Emmons cyclization, regioselective protection of the C-5-hydroxy group, and oxidation of the C-3-hydroxy group, is described. In this synthesis, the conformational analysis by NMR played mt important role.