(1R,6S)-2-O-acetyl-1,4-anhydro-3,5,6-trideoxy-1-(3-oxopropyl)-6-methyl-2-C-methyl-5-methylene-7-O-(triisopropylsilyl)-D-xylo-heptitol | 1006701-63-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,6S)-2-O-acetyl-1,4-anhydro-3,5,6-trideoxy-1-(3-oxopropyl)-6-methyl-2-C-methyl-5-methylene-7-O-(triisopropylsilyl)-D-xylo-heptitol
• CAS: 1006701-63-8
• 化学式: C₂₄H₄₄O₅Si
• 分子量: 440.696
• InChiKey: BJOSKSIJBKHTAO-OTUUDDROSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.83
• 重原子数：
  30.0
• 可旋转键数：
  12.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  61.83
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (1R,6S)-2-O-acetyl-1,4-anhydro-3,5,6-trideoxy-1-(3-oxopropyl)-6-methyl-2-C-methyl-5-methylene-7-O-(triisopropylsilyl)-D-xylo-heptitol 在 sodium chlorite 作用下， 以 水 、 叔丁醇 为溶剂， 反应 1.5h， 生成 3-[(2R,3R,5R)-3-Acetoxy-3-methyl-5-((S)-2-methyl-1-methylene-3-triisopropylsilanyloxy-propyl)-tetrahydro-furan-2-yl]-propionic acid
  参考文献：
  名称：

  Stereoselective Construction of the Tricyclic Core of Neoliacinic Acid

  摘要：

  [GRAPHICS]The tricyclic core of the plant-derived sesquiterpene natural product neoliacinic acid was synthesized using a novel synthetic strategy. The pivotal synthetic transformations are construction of the key bicyclic ether-bridged intermediate by sequential deployment of metal carbenoid C-H insertion and ylide-forming reactions and installation of the lactone portion of neoliacinic acid by an acid-catalyzed intramolecular ring-opening reaction of an epoxide with a carboxylic acid.

  DOI：

  10.1021/jo702111u
• 作为产物：
  描述：

  (1R,6S)-2-O-acetyl-1,4-anhydro-3,5,6-trideoxy-1-(3-hydroxypropyl)-6-methyl-2-C-methyl-5-methylene-7-O-(triisopropylsilyl)-D-xylo-heptitol 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以93%的产率得到(1R,6S)-2-O-acetyl-1,4-anhydro-3,5,6-trideoxy-1-(3-oxopropyl)-6-methyl-2-C-methyl-5-methylene-7-O-(triisopropylsilyl)-D-xylo-heptitol
  参考文献：
  名称：

  Stereoselective Construction of the Tricyclic Core of Neoliacinic Acid

  摘要：

  [GRAPHICS]The tricyclic core of the plant-derived sesquiterpene natural product neoliacinic acid was synthesized using a novel synthetic strategy. The pivotal synthetic transformations are construction of the key bicyclic ether-bridged intermediate by sequential deployment of metal carbenoid C-H insertion and ylide-forming reactions and installation of the lactone portion of neoliacinic acid by an acid-catalyzed intramolecular ring-opening reaction of an epoxide with a carboxylic acid.

  DOI：

  10.1021/jo702111u