[2-azido-2-(4-benzyloxy-2,6-dichloro-phenyl)-ethoxy]-tert-butyl-dimethyl-silane | 461031-83-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: [2-azido-2-(4-benzyloxy-2,6-dichloro-phenyl)-ethoxy]-tert-butyl-dimethyl-silane
• 英文别名: [(2R)-2-azido-2-(2,6-dichloro-4-phenylmethoxyphenyl)ethoxy]-tert-butyl-dimethylsilane
• CAS: 461031-83-4
• 化学式: C₂₁H₂₇Cl₂N₃O₂Si
• 分子量: 452.456
• InChiKey: RJSMFXNSUMDLBC-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.95
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  32.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [2-azido-2-(4-benzyloxy-2,6-dichloro-phenyl)-ethoxy]-tert-butyl-dimethyl-silane 在 palladium on activated charcoal 四丁基氟化铵 、 氢气 、 碳酸氢钠 、 对甲苯磺酸 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 、 乙酸乙酯 为溶剂， 反应 43.0h， 生成 (4S)-N-(tert-butoxycarbonyl)-2,2'-dimethyl-4-[(4-hydroxy)-2,6-dichlorophenyl]-1,3-oxazoline
  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
• 作为产物：
  描述：

  1-[4-(benzyloxy)-2,6-dichlorophenyl]-2-(tert-butyldimethylsilyl)oxy-1-ethylalcohol 在 偶氮二甲酸二异丙酯 、 二苯基膦叠氮化物 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 10.0h， 生成 (S)-[2-azido-2-(4-benzyloxy-2,6-dichloro-phenyl)-ethoxy]-tert-butyl-dimethyl-silane 、 [2-azido-2-(4-benzyloxy-2,6-dichloro-phenyl)-ethoxy]-tert-butyl-dimethyl-silane
  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