(R)-2-{(4S,5R,6S)-6-[(1S,3R)-5-(Dimethoxy-phosphoryl)-1,3-dimethyl-4-oxo-pentyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-propionic acid | 205178-68-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: (R)-2-{(4S,5R,6S)-6-[(1S,3R)-5-(Dimethoxy-phosphoryl)-1,3-dimethyl-4-oxo-pentyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-propionic acid
• 英文别名: (2R)-2-[(4S,5R,6S)-6-[(2S,4R)-6-dimethoxyphosphoryl-4-methyl-5-oxohexan-2-yl]-2,2,5-trimethyl-1,3-dioxan-4-yl]propanoic acid
• CAS: 205178-68-3
• 化学式: C₁₉H₃₅O₈P
• 分子量: 422.456
• InChiKey: KXAOZYGMQAXKGX-WQXBFISLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (R)-2-{(4S,5R,6S)-6-[(1S,3R)-5-(Dimethoxy-phosphoryl)-1,3-dimethyl-4-oxo-pentyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-propionic acid 在 盐酸 、 4-二甲氨基吡啶 、 18-冠醚-6 、 2,4,6-三氯苯甲酰氯 、 camphor-10-sulfonic acid 、 potassium carbonate 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 11.5h， 生成 (3R,4S,5R,6S,7S,9R,13R,14R)-13-benzyloxy-14-ethyl-4-hydroxy-6-(4-methoxybenzyloxy)-3,5,7,9,13-pentamethyl-1-oxacyclotetradec-11(E)-ene-2,10-dione
  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：

  (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 在 potassium permanganate 、 sodium periodate 、 碳酸氢钠 作用下， 以 丙酮 为溶剂， 以80%的产率得到(R)-2-{(4S,5R,6S)-6-[(1S,3R)-5-(Dimethoxy-phosphoryl)-1,3-dimethyl-4-oxo-pentyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-propionic acid
  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.