(1S,3R,5R,7R)-8-Chloro-1,5-di-C-cyano-1,3:5,7-bis-O-(1-methylethylidene)-1,3,5,7-octanetetrol | 139100-49-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,3R,5R,7R)-8-Chloro-1,5-di-C-cyano-1,3:5,7-bis-O-(1-methylethylidene)-1,3,5,7-octanetetrol
• 英文别名: (4R,6R)-6-(chloromethyl)-4-[[(4R,6S)-6-cyano-2,2-dimethyl-1,3-dioxan-4-yl]methyl]-2,2-dimethyl-1,3-dioxane-4-carbonitrile
• CAS: 139100-49-5
• 化学式: C₁₆H₂₃ClN₂O₄
• 分子量: 342.823
• InChiKey: QOWDBEAYGOCECS-OQMKEHIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 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：

  (1S,3R,5R,7R)-8-Chloro-1,5-di-C-cyano-1,3:5,7-bis-O-(1-methylethylidene)-1,3,5,7-octanetetrol 在 N,N-二甲基丙烯基脲 、 18-冠醚-6 、 lithium diethylamide 、 双(三甲基硅烷基)氨基钾 、 potassium iodide 作用下， 以 四氢呋喃 、 甲苯 、 xylene 为溶剂， 反应 48.0h， 生成 (2R,4R,6R,8S,10R,12S,14R,16R)-1-Chloro-4,8,12,16-tetra-C-cyano-2,4:6,8:10,12:14,16-tetrakis-O-(1-methylethylidene)-18-nonadecene-2,4,6,8,10,12,14,16-octol
  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：

  2,2-二甲氧基丙烷 在 N,N-二甲基丙烯基脲 、 lithium diethylamide 作用下， 反应 4.0h， 生成 (1S,3R,5R,7R)-8-Chloro-1,5-di-C-cyano-1,3:5,7-bis-O-(1-methylethylidene)-1,3,5,7-octanetetrol
  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.