(3R,5R)-2-Bromo-3-hydroxy-2,6-dimethyl-5-trimethylsilanyloxy-heptanoic acid ethyl ester | 274905-26-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: (3R,5R)-2-Bromo-3-hydroxy-2,6-dimethyl-5-trimethylsilanyloxy-heptanoic acid ethyl ester
• 英文别名: ethyl (3R,5R)-2-bromo-3-hydroxy-2,6-dimethyl-5-trimethylsilyloxyheptanoate
• CAS: 274905-26-9
• 化学式: C₁₄H₂₉BrO₄Si
• 分子量: 369.371
• InChiKey: PIUGRTRSGCBBFG-QAYQGLBKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.33
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3R,5R)-2-Bromo-3-hydroxy-2,6-dimethyl-5-trimethylsilanyloxy-heptanoic acid ethyl ester 在 三乙基硼 、 三正丁基氢锡 、 柠檬酸 作用下， 以 甲醇 、 丙酮 、 甲苯 为溶剂， 反应 0.33h， 生成 ethyl (2R,3R,5R)-3,5-isopropylidenedioxy-2,6-dimethylheptanoate
  参考文献：
  名称：

  An efficient method for the synthesis of enantiopure 2,3-anti-propionate aldols involving a 3,5-syn- or anti-diol subunit through chiral borane-mediated enantioselective aldol reaction coupled with radical reduction

  摘要：

  2,3-anti-Propionate aldols involving a 3,5-syn- or anti-diol subunit, versatile enantiopure segments available for macrolide synthesis, were prepared by a chiral oxazaborolidinone-promoted asymmetric aldol reaction with 2-bromo-1-ethoxy-2-methyl-1-trimethylsiloxyethene and the following highly anti-preferential radical debromination. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00234-3
• 作为产物：
  描述：

  ethyl (3R)-3-hydroxy-4-methylpentanoate 在 2,6-二甲基吡啶 、 chiral-TsNBHOCOCH(iPr) 、 二异丁基氢化铝 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 生成 (3R,5R)-2-Bromo-3-hydroxy-2,6-dimethyl-5-trimethylsilanyloxy-heptanoic acid ethyl ester
  参考文献：
  名称：

  An efficient method for the synthesis of enantiopure 2,3-anti-propionate aldols involving a 3,5-syn- or anti-diol subunit through chiral borane-mediated enantioselective aldol reaction coupled with radical reduction

  摘要：

  2,3-anti-Propionate aldols involving a 3,5-syn- or anti-diol subunit, versatile enantiopure segments available for macrolide synthesis, were prepared by a chiral oxazaborolidinone-promoted asymmetric aldol reaction with 2-bromo-1-ethoxy-2-methyl-1-trimethylsiloxyethene and the following highly anti-preferential radical debromination. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00234-3

文献信息

• An efficient method for the synthesis of enantiopure 2,3-anti-propionate aldols involving a 3,5-syn- or anti-diol subunit through chiral borane-mediated enantioselective aldol reaction coupled with radical reduction
  作者：Syun-ichi Kiyooka、Kazi A Shahid

  DOI：10.1016/s0040-4039(00)00234-3

  日期：2000.4

  2,3-anti-Propionate aldols involving a 3,5-syn- or anti-diol subunit, versatile enantiopure segments available for macrolide synthesis, were prepared by a chiral oxazaborolidinone-promoted asymmetric aldol reaction with 2-bromo-1-ethoxy-2-methyl-1-trimethylsiloxyethene and the following highly anti-preferential radical debromination. (C) 2000 Elsevier Science Ltd. All rights reserved.