(E)-(2S,3R,4S)-6-Cyclohexyl-3-methoxymethoxy-2,4-dimethyl-hex-5-en-1-ol | 909193-82-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (E)-(2S,3R,4S)-6-Cyclohexyl-3-methoxymethoxy-2,4-dimethyl-hex-5-en-1-ol
• 英文别名: (E,2S,3R,4S)-6-cyclohexyl-3-(methoxymethoxy)-2,4-dimethylhex-5-en-1-ol
• CAS: 909193-82-4
• 化学式: C₁₆H₃₀O₃
• 分子量: 270.412
• InChiKey: VDXAMECESFVTEV-HNMZYKETSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-(2S,3R,4S)-6-Cyclohexyl-3-methoxymethoxy-2,4-dimethyl-hex-5-en-1-ol 在 sodium hexamethyldisilazane 、 四丁基碘化铵 、 sodium hydride 、 臭氧 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.17h， 生成 1-(((2S,3R,4S,Z)-6-iodo-3-(methoxymethoxy)-2,4-dimethylhept-5-enyloxy)methyl)-4-methoxybenzene
  参考文献：
  名称：

  Scalable, Catalytic Asymmetric Synthesis of Syn, Anti Stereotriad Building Blocks for Polypropionate Antibiotics

  摘要：

  Asymmetric catalysis and chirality transfer by the 2,3-Wittig rearrangement were combined to provide a syn, anti stereotriad-containing olefinic alcohol in five steps from inexpensive starting materials. Development of this compound, a versatile intermediate for polypropionate synthesis, gave known building blocks for discodermolide.

  DOI：

  10.1021/ol0612612
• 作为产物：
  描述：

  [(1E,3S,4R)-4-(methoxymethoxy)-3,5-dimethylhexa-1,5-dienyl]cyclohexane 在 9-borabicyclo[3.3.1]nonane dimer 、 sodium hydroxide 、 双氧水 作用下， 以 四氢呋喃 为溶剂， 以92%的产率得到(E)-(2S,3R,4S)-6-Cyclohexyl-3-methoxymethoxy-2,4-dimethyl-hex-5-en-1-ol
  参考文献：
  名称：

  Scalable, Catalytic Asymmetric Synthesis of Syn, Anti Stereotriad Building Blocks for Polypropionate Antibiotics

  摘要：

  Asymmetric catalysis and chirality transfer by the 2,3-Wittig rearrangement were combined to provide a syn, anti stereotriad-containing olefinic alcohol in five steps from inexpensive starting materials. Development of this compound, a versatile intermediate for polypropionate synthesis, gave known building blocks for discodermolide.

  DOI：

  10.1021/ol0612612

文献信息

• INTERMEDIATES FOR THE SYNTHESIS OF POLYPROPIONATE ANTIBIOTICS
  申请人：Parker Kathlyn

  公开号：US20070282121A1

  公开（公告）日：2007-12-06

  The invention relates to intermediate compounds of the formula wherein R 1 is H or a protecting group, R 2 and R 3 each independently represent H, methyl, or a leaving group, provided that at least one, but not both, of R 2 and R 3 is a leaving group. The intermediate compounds are useful for the synthesis of discodermolide, its derivatives, and related compounds.
• US7297807B1
  申请人：——

  公开号：US7297807B1

  公开（公告）日：2007-11-20
• US7339066B1
  申请人：——

  公开号：US7339066B1

  公开（公告）日：2008-03-04
• Scalable, Catalytic Asymmetric Synthesis of Syn, Anti Stereotriad Building Blocks for Polypropionate Antibiotics
  作者：Kathlyn A. Parker、Huanyan Cao

  DOI：10.1021/ol0612612

  日期：2006.8.1

  Asymmetric catalysis and chirality transfer by the 2,3-Wittig rearrangement were combined to provide a syn, anti stereotriad-containing olefinic alcohol in five steps from inexpensive starting materials. Development of this compound, a versatile intermediate for polypropionate synthesis, gave known building blocks for discodermolide.