tert-butyl-[(3R,4S,5E)-6-cyclohexyl-2,4-dimethylhexa-1,5-dien-3-yl]oxy-dimethylsilane | 909193-79-9

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: tert-butyl-[(3R,4S,5E)-6-cyclohexyl-2,4-dimethylhexa-1,5-dien-3-yl]oxy-dimethylsilane
• CAS: 909193-79-9
• 化学式: C₂₀H₃₈OSi
• 分子量: 322.607
• InChiKey: HDPKHNVVLFWBOZ-DPDJIQLXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.73
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  tert-butyl-[(3R,4S,5E)-6-cyclohexyl-2,4-dimethylhexa-1,5-dien-3-yl]oxy-dimethylsilane 在 manganese(IV) oxide 、 9-borabicyclo[3.3.1]nonane dimer 、 臭氧 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 73.0h， 生成 (3R,4S,5S)-4-[(tert-butyldimethylsilanyl)oxy]-3,5-dimethyltetrahydropyran-2-one
  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：

  (S)(Z)-{1-[(2-methylallyl)oxy]but-2-en-1-yl}cyclohexane 在 2,6-二甲基吡啶 、 正丁基锂 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 15.5h， 生成 tert-butyl-[(3R,4S,5E)-6-cyclohexyl-2,4-dimethylhexa-1,5-dien-3-yl]oxy-dimethylsilane
  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：The Research Foundation of State University of New York

  公开号：US07297807B1

  公开（公告）日：2007-11-20

  The invention relates to intermediate compounds of the formula wherein R1 is H or a protecting group, R2 and R3 each independently represent H, methyl, or a leaving group, provided that at least one, but not both, of R2 and R3 is a leaving group. The intermediate compounds are useful for the synthesis of discodermolide, its derivatives, and related compounds.

  这项发明涉及公式中的中间化合物 其中R1为H或保护基团，R2和R3分别独立地代表H、甲基或脱离基团，但要求R2和R3中至少有一个而不是两个是脱离基团。这些中间化合物可用于合成discodermolide、其衍生物和相关化合物。
• 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.