(3R,4S,5S)-4-[(tert-butyldimethylsilanyl)oxy]-3,5-dimethyltetrahydropyran-2-ol | 443761-67-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: (3R,4S,5S)-4-[(tert-butyldimethylsilanyl)oxy]-3,5-dimethyltetrahydropyran-2-ol
• 英文别名: (3R,4S,5S)-4-[tert-butyl(dimethyl)silyl]oxy-3,5-dimethyloxan-2-ol
• CAS: 443761-67-9
• 化学式: C₁₃H₂₈O₃Si
• 分子量: 260.449
• InChiKey: RYSFJNOHYQLZCR-PSIUFMSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.0
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  (3R,4S,5S)-4-[(tert-butyldimethylsilanyl)oxy]-3,5-dimethyltetrahydropyran-2-ol 在 manganese(IV) oxide 作用下， 以 乙酸乙酯 为溶剂， 反应 48.0h， 以23.7 mg的产率得到(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：

  (3R,4S)(E)-6-cyclohexyl-2,4-dimethylhexa-1,5-dien-3-ol 在 2,6-二甲基吡啶 、 9-borabicyclo[3.3.1]nonane dimer 、 臭氧 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 26.5h， 生成 (3R,4S,5S)-4-[(tert-butyldimethylsilanyl)oxy]-3,5-dimethyltetrahydropyran-2-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

• A Practical Building Block for the Synthesis of Discodermolide
  作者：Olivier Loiseleur、Guido Koch、Trixie Wagner

  DOI：10.1021/op049950l

  日期：2004.7.1

  A new highly diastereoselective and practical route to the lactone 6a which is used as a key building block for the total synthesis of the microtubule-stabilizing anticancer agent discodermolide is reported. This exploits the chiral auxiliary (4R)4-isopropyl-5,5-diphenyloxazolidin-2-one (7) which conveys crystallinity to the synthetic intermediates throughout the entire process. Purifications can thus be performed by recrystallization, avoiding chromatography to afford the final product in high enantiomeric purity. The overall efficiency is augmented by the facile recovery of the auxiliary by precipitation at the end of the sequence.
• 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.