(1S)-1-[4-(benzyloxy)-2,6-dichlorophenyl]-2-(tert-butyldimethylsilyl)oxy-1-ethylalcohol | 461031-82-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1S)-1-[4-(benzyloxy)-2,6-dichlorophenyl]-2-(tert-butyldimethylsilyl)oxy-1-ethylalcohol
• 英文别名: (1S)-2-[tert-butyl(dimethyl)silyl]oxy-1-(2,6-dichloro-4-phenylmethoxyphenyl)ethanol
• CAS: 461031-82-3
• 化学式: C₂₁H₂₈Cl₂O₃Si
• 分子量: 427.443
• InChiKey: GRURJQJJJGOXED-LJQANCHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.63
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3,5-二氯苯酚 在 咪唑 、 4-二甲氨基吡啶 、 AD-mix-α 、 正丁基锂 、 水 、 仲丁基锂 、 potassium carbonate 、 三乙胺 、 potassium iodide 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 环己烷 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 74.33h， 生成 (1S)-1-[4-(benzyloxy)-2,6-dichlorophenyl]-2-(tert-butyldimethylsilyl)oxy-1-ethylalcohol
  参考文献：
  名称：

  On the Verge of Axial Chirality:  Atroposelective Synthesis of the AB-Biaryl Fragment of Vancomycin^,

  摘要：

  [GRAPHIC]Using the "lactone concept", differently substituted AB-biaryl fragments (P)-2 (R = Me, t-Bu) of vancomycin have been synthesized atroposelectively. Their otherwise configurational instability was remedied by inclusion of two chlorine atoms in the B ring to give (M)-29. Starting from a still configurationally unstable lactone-bridged precursor, we obtained this biaryl with high atroposelectivity (dr 94:6) by ring cleavage with dynamic kinetic diastereomeric resolution.

  DOI：

  10.1021/ol026182e

文献信息

• On the Verge of Axial Chirality:  Atroposelective Synthesis of the AB-Biaryl Fragment of Vancomycin^,
  作者：Gerhard Bringmann、Dirk Menche、Jörg Mühlbacher、Matthias Reichert、Nozomi Saito、Steven S. Pfeiffer、Bruce H. Lipshutz

  DOI：10.1021/ol026182e

  日期：2002.8.1

  [GRAPHIC]Using the "lactone concept", differently substituted AB-biaryl fragments (P)-2 (R = Me, t-Bu) of vancomycin have been synthesized atroposelectively. Their otherwise configurational instability was remedied by inclusion of two chlorine atoms in the B ring to give (M)-29. Starting from a still configurationally unstable lactone-bridged precursor, we obtained this biaryl with high atroposelectivity (dr 94:6) by ring cleavage with dynamic kinetic diastereomeric resolution.