(2R,4R,6R,8R)-1-Chloro-4,8-di-C-cyano-2,4:6,8-bis-O-(1-methylethylidene)-10-eicosene-2,4,6,8-tetrol | 139100-50-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,4R,6R,8R)-1-Chloro-4,8-di-C-cyano-2,4:6,8-bis-O-(1-methylethylidene)-10-eicosene-2,4,6,8-tetrol
• 英文别名: (4R,6R)-6-[[(4R,6R)-6-(chloromethyl)-4-cyano-2,2-dimethyl-1,3-dioxan-4-yl]methyl]-2,2-dimethyl-4-prop-2-enyl-1,3-dioxane-4-carbonitrile
• CAS: 139100-50-8
• 化学式: C₁₉H₂₇ClN₂O₄
• 分子量: 382.887
• InChiKey: JLPYLHCZOCLFRU-OHDICMOHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  84.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2R,4R,6R,8R)-1-Chloro-4,8-di-C-cyano-2,4:6,8-bis-O-(1-methylethylidene)-10-eicosene-2,4,6,8-tetrol 在 18-冠醚-6 、 potassium iodide 作用下， 以 xylene 为溶剂， 反应 48.0h， 以89%的产率得到(2R,4R,6R,8R)-4,8-Di-C-cyano-1-iodo-2,4:6,8-bis-O-(1-methylethylidene)-10-eicosene-2,4,6,8-tetrol
  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-(Chloromethyl)-2,2-dimethyl-1,3-dioxane-6-carbonitrile 在 N,N-二甲基丙烯基脲 、 lithium diethylamide 、 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 4.0h， 生成 (2R,4R,6R,8R)-1-Chloro-4,8-di-C-cyano-2,4:6,8-bis-O-(1-methylethylidene)-10-eicosene-2,4,6,8-tetrol
  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

文献信息

• An iterative and convergent synthesis of syn polyols
  作者：Scott D. Rychnovsky、George Griesgraber

  DOI：10.1021/jo00031a041

  日期：1992.2

  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.