(10S,12S)-10-[1-(tert-butyl)-1,1-diphenylsilyl]oxy-5-hydroxy-12-methyl-1-oxacyclododecan-2-one | 1041994-02-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯类和类似物
• 英文名称: (10S,12S)-10-[1-(tert-butyl)-1,1-diphenylsilyl]oxy-5-hydroxy-12-methyl-1-oxacyclododecan-2-one
• CAS: 1041994-02-8
• 化学式: C₂₈H₄₀O₄Si
• 分子量: 468.709
• InChiKey: ZBBAYJUNCWTSGT-OTKIHZFJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.97
• 重原子数：
  33.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  55.76
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (10S,12S)-10-[1-(tert-butyl)-1,1-diphenylsilyl]oxy-5-hydroxy-12-methyl-1-oxacyclododecan-2-one 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以90%的产率得到(10S,12S)-10-[1-(tert-butyl)-1,1-diphenylsilyl]oxy-12-methyl-1-oxacyclododecane-2,5-dione
  参考文献：
  名称：

  The first synthesis of a 12-membered macrolide natural product via a RCM protocol: determination of absolute stereochemistry

  摘要：

  The first synthesis of (10S,12R)-10-hydroxy-12-methyl-1-oxacyclododecane-2,5-dione and its C12 epimer is reported, thereby assigning the absolute stereochemistry of the natural product. The strategy utilizes a syn selective reduction, Yamaguchi esterification, and ring-closing metathesis as the key steps. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.04.016
• 作为产物：
  描述：

  (10S,12S)-5-[1-(benzyloxy)]-10-[1-(tert-butyl)-1,1-diphenylsilyl]oxy-12-methyl-1-oxa-7-cyclododecen-2-one 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 6.0h， 以82%的产率得到(10S,12S)-10-[1-(tert-butyl)-1,1-diphenylsilyl]oxy-5-hydroxy-12-methyl-1-oxacyclododecan-2-one
  参考文献：
  名称：

  The first synthesis of a 12-membered macrolide natural product via a RCM protocol: determination of absolute stereochemistry

  摘要：

  The first synthesis of (10S,12R)-10-hydroxy-12-methyl-1-oxacyclododecane-2,5-dione and its C12 epimer is reported, thereby assigning the absolute stereochemistry of the natural product. The strategy utilizes a syn selective reduction, Yamaguchi esterification, and ring-closing metathesis as the key steps. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.04.016