2-Bromo-2-((4R,6R)-6-isopropyl-2,2-dimethyl-[1,3]dioxan-4-yl)-propionic acid ethyl ester | 274905-30-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-Bromo-2-((4R,6R)-6-isopropyl-2,2-dimethyl-[1,3]dioxan-4-yl)-propionic acid ethyl ester
• 英文别名: ethyl 2-bromo-2-[(4R,6R)-2,2-dimethyl-6-propan-2-yl-1,3-dioxan-4-yl]propanoate
• CAS: 274905-30-5
• 化学式: C₁₄H₂₅BrO₄
• 分子量: 337.254
• InChiKey: LCEAPKZHJMVNOI-HRQHSXBYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.93
• 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-Bromo-2-((4R,6R)-6-isopropyl-2,2-dimethyl-[1,3]dioxan-4-yl)-propionic acid ethyl ester 在 三乙基硼 、 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 以92%的产率得到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 、 柠檬酸 作用下， 以 甲醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 20.33h， 生成 2-Bromo-2-((4R,6R)-6-isopropyl-2,2-dimethyl-[1,3]dioxan-4-yl)-propionic 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.