(4S,6S,8S,10R,12R)-6,8:10,12-bis-O-(1-methylethylidene)-1-heptadecene-4,6,8,10,12-pentaol | 195007-99-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4S,6S,8S,10R,12R)-6,8:10,12-bis-O-(1-methylethylidene)-1-heptadecene-4,6,8,10,12-pentaol
• 英文别名: (2S)-1-[(4S,6S)-6-[[(4R,6R)-2,2-dimethyl-6-pentyl-1,3-dioxan-4-yl]methyl]-2,2-dimethyl-1,3-dioxan-4-yl]pent-4-en-2-ol
• CAS: 195007-99-9
• 化学式: C₂₃H₄₂O₅
• 分子量: 398.583
• InChiKey: NKJSJKSBMBNQJY-LUYSREMJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (2R,4R,6R,8R)-1-chloromercury-2,4:6,8-bis-O-(1-methylethylidene)-tridecane-2,4,6,8-tetraol 在 acetylacetonatodicarbonylrhodium(l) 三乙烯二胺 、 2-叔丁基苯酚亚磷酸盐 、 氢气 作用下， 以 乙醚 、 乙酸乙酯 为溶剂， -78.0~50.0 ℃ 、5.52 MPa 条件下， 生成 (4S,6S,8S,10R,12R)-6,8:10,12-bis-O-(1-methylethylidene)-1-heptadecene-4,6,8,10,12-pentaol
  参考文献：
  名称：

  Rhodium-Catalyzed Formylation of Organomercurials:  Application to Efficient Polyol Synthesis

  摘要：

  [GRAPHICS]The rhodium-catalyzed formylation of organomercurials-a new transformation of organomercurials-is reported. The addition of 0.50 equiv of 1,4-diazabicyclo[2.2.2]octane (DABCO) was found to promote the reaction, and it is postulated that the DABCO acts as a ligand for mercury. Several examples are presented to document the scope of the reaction. This reaction was developed in the context of a larger program focused on the development of efficient strategies for the synthesis of polyol-derived natural products, and an efficient (8 steps) synthesis of Tolypothrix pentaether that employs this methodology is reported.

  DOI：

  10.1021/ol006393o

文献信息

• Rhodium-Catalyzed Formylation of Organomercurials:  Application to Efficient Polyol Synthesis
  作者：Stella T. Sarraf、James L. Leighton

  DOI：10.1021/ol006393o

  日期：2000.10.1

  [GRAPHICS]The rhodium-catalyzed formylation of organomercurials-a new transformation of organomercurials-is reported. The addition of 0.50 equiv of 1,4-diazabicyclo[2.2.2]octane (DABCO) was found to promote the reaction, and it is postulated that the DABCO acts as a ligand for mercury. Several examples are presented to document the scope of the reaction. This reaction was developed in the context of a larger program focused on the development of efficient strategies for the synthesis of polyol-derived natural products, and an efficient (8 steps) synthesis of Tolypothrix pentaether that employs this methodology is reported.