ethyl (2S,3R)-3-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-fluoro-3-hydroxy-2-methylpropanoate | 1033394-86-3

• 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: ethyl (2S,3R)-3-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-fluoro-3-hydroxy-2-methylpropanoate
• CAS: 1033394-86-3
• 化学式: C₁₁H₁₉FO₅
• 分子量: 250.267
• InChiKey: BNQCBWJKDHRWAG-XLDPMVHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-氟丙酸乙酯 、 (R)-(+)-2,2-二甲基-1,3-二氧戊环-4-甲醛 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 生成 ethyl (2S,3R)-3-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-fluoro-3-hydroxy-2-methylpropanoate 、 ethyl (2S,3S)-3-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-fluoro-3-hydroxy-2-methylpropanoate 、 (2R,3R)-ethyl-3-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-fluoro-2-methyl-3-hydroxy propionate
  参考文献：
  名称：

  A practical synthesis of (2R)-3,5-di-O-benzoyl-2-fluoro-2-C-methyl-d-ribono-γ-lactone

  摘要：

  The title compound was synthesized in 23% overall yield using only one purification in four chemical steps. The key features of this practical synthesis include an asymmetric aldol condensation and an enzymatic hydrolysis to remove the major undesired isomer. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.02.006

文献信息

• WO2008/74693
  申请人：——

  公开号：——

  公开（公告）日：——
• A practical synthesis of (2R)-3,5-di-O-benzoyl-2-fluoro-2-C-methyl-d-ribono-γ-lactone
  作者：Pingsheng Zhang、Hans Iding、Miall Cedilote、Stephan Brunner、Thomas Williamson、Thomas P. Cleary

  DOI：10.1016/j.tetasy.2009.02.006

  日期：2009.2

  The title compound was synthesized in 23% overall yield using only one purification in four chemical steps. The key features of this practical synthesis include an asymmetric aldol condensation and an enzymatic hydrolysis to remove the major undesired isomer. (C) 2009 Elsevier Ltd. All rights reserved.