2-[(2S,3S,4S,5R,6S)-4,6-bis[[tert-butyl(dimethyl)silyl]oxy]-3,5-dimethyloxan-2-yl]acetaldehyde | 957267-14-0

• 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: 2-[(2S,3S,4S,5R,6S)-4,6-bis[[tert-butyl(dimethyl)silyl]oxy]-3,5-dimethyloxan-2-yl]acetaldehyde
• CAS: 957267-14-0
• 化学式: C₂₁H₄₄O₄Si₂
• 分子量: 416.749
• InChiKey: JUMJPAZPTWWJDY-PJVZLEMVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.98
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  、 2-[(2S,3S,4S,5R,6S)-4,6-bis[[tert-butyl(dimethyl)silyl]oxy]-3,5-dimethyloxan-2-yl]acetaldehyde 在 正丁基锂 作用下， 以 正己烷 、 四氢呋喃 为溶剂， 反应 1.0h， 以64%的产率得到
  参考文献：
  名称：

  Short Synthesis of the C1−C14 Stretch of Discodermolide from Building Blocks Prepared by Asymmetric Catalysis

  摘要：

  A convergent and stereoselective synthesis of the C1-C14 stretch of (+)-discodermolide demonstrates the utility of the "asymmetric catalysis approach" to complex polypropionates. The preparation of this complex synthon requires 15 steps in the longest linear sequence and 19 steps total from inexpensive materials.

  DOI：

  10.1021/ol7029933
• 作为产物：
  描述：

  2-[(2S,3S,4S,5R)-4-[tert-butyl(dimethyl)silyl]oxy-6-hydroxy-3,5-dimethyloxan-2-yl]acetaldehyde 、 叔丁基二甲基氯硅烷 在 咪唑 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以70%的产率得到2-[(2S,3S,4S,5R,6S)-4,6-bis[[tert-butyl(dimethyl)silyl]oxy]-3,5-dimethyloxan-2-yl]acetaldehyde
  参考文献：
  名称：

  Short Synthesis of the C1−C14 Stretch of Discodermolide from Building Blocks Prepared by Asymmetric Catalysis

  摘要：

  A convergent and stereoselective synthesis of the C1-C14 stretch of (+)-discodermolide demonstrates the utility of the "asymmetric catalysis approach" to complex polypropionates. The preparation of this complex synthon requires 15 steps in the longest linear sequence and 19 steps total from inexpensive materials.

  DOI：

  10.1021/ol7029933

文献信息

• Short Synthesis of the C1−C14 Stretch of Discodermolide from Building Blocks Prepared by Asymmetric Catalysis
  作者：Huanyan Cao、Kathlyn A. Parker

  DOI：10.1021/ol7029933

  日期：2008.4.1

  A convergent and stereoselective synthesis of the C1-C14 stretch of (+)-discodermolide demonstrates the utility of the "asymmetric catalysis approach" to complex polypropionates. The preparation of this complex synthon requires 15 steps in the longest linear sequence and 19 steps total from inexpensive materials.