(4R,6R,8S,10R,12S,14R,16S,18R,20S,22S)-4,8,12,16,20-Penta-C-cyano-4,6:8,10:12,14:16,18:20,22-pentakis-O-(1-methylethylidene)-1-heptacosene-4,6,8,10,12,14,16,18,20,22-decol | 139071-32-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4R,6R,8S,10R,12S,14R,16S,18R,20S,22S)-4,8,12,16,20-Penta-C-cyano-4,6:8,10:12,14:16,18:20,22-pentakis-O-(1-methylethylidene)-1-heptacosene-4,6,8,10,12,14,16,18,20,22-decol
• 英文别名: (4S,6S)-4-[[(4R,6S)-6-cyano-6-[[(4R,6S)-6-cyano-6-[[(4R,6S)-6-cyano-6-[[(4R,6R)-6-cyano-2,2-dimethyl-6-prop-2-enyl-1,3-dioxan-4-yl]methyl]-2,2-dimethyl-1,3-dioxan-4-yl]methyl]-2,2-dimethyl-1,3-dioxan-4-yl]methyl]-2,2-dimethyl-1,3-dioxan-4-yl]methyl]-2,2-dimethyl-6-pentyl-1,3-dioxane-4-carbonitrile
• CAS: 139071-32-2
• 化学式: C₄₇H₆₉N₅O₁₀
• 分子量: 864.092
• InChiKey: DJNMZLKGDCHWTA-OHVTUXJFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  62
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  211
• 氢给体数：
  0
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  (4R,6R,8S,10R,12S,14R,16S,18R,20S,22S)-4,8,12,16,20-Penta-C-cyano-4,6:8,10:12,14:16,18:20,22-pentakis-O-(1-methylethylidene)-1-heptacosene-4,6,8,10,12,14,16,18,20,22-decol 在 氨 、 lithium 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以85%的产率得到(4R,6R,8S,10R,12S,14R,16S,18R,20S,22S)-4,6:8,10:12,14:16,18:20,22-Pentakis-O-(1-methylethylidene)-1-heptacosene-4,6,8,10,12,14,16,18,20,22-decol
  参考文献：
  名称：

  An iterative and convergent synthesis of syn polyols

  摘要：

  We have developed a new iterative and convergent synthesis of alternating (1,3,5...) polyol chains based on enantiomerically enriched (94% ee) chloro nitrile 1. Chloro nitrile 1 is both a potential nucleophile and a potential electrophile; orthogonal nucleophilic or electrophilic activation leads to a highly efficient synthetic strategy for alternating polyol chains. As an illustration permethylated polyol 2 (n = 10), a natural product with 10 stereogenic centers isolated from the blue green alga Tolypothrix conglutinata var. chlorata, was prepared in 10 steps from 1.

  DOI：

  10.1021/jo00031a041
• 作为产物：
  描述：

  (4R)-4-(Iodomethyl)-2,2-dimethyl-1,3-dioxane-6-carbonitrile 在 N,N-二甲基丙烯基脲 、 18-冠醚-6 、 lithium diethylamide 、 potassium iodide 作用下， 以 四氢呋喃 、 xylene 为溶剂， 反应 48.0h， 生成 (4R,6R,8S,10R,12S,14R,16S,18R,20S,22S)-4,8,12,16,20-Penta-C-cyano-4,6:8,10:12,14:16,18:20,22-pentakis-O-(1-methylethylidene)-1-heptacosene-4,6,8,10,12,14,16,18,20,22-decol
  参考文献：
  名称：

  An iterative and convergent synthesis of syn polyols

  摘要：

  We have developed a new iterative and convergent synthesis of alternating (1,3,5...) polyol chains based on enantiomerically enriched (94% ee) chloro nitrile 1. Chloro nitrile 1 is both a potential nucleophile and a potential electrophile; orthogonal nucleophilic or electrophilic activation leads to a highly efficient synthetic strategy for alternating polyol chains. As an illustration permethylated polyol 2 (n = 10), a natural product with 10 stereogenic centers isolated from the blue green alga Tolypothrix conglutinata var. chlorata, was prepared in 10 steps from 1.

  DOI：

  10.1021/jo00031a041