(R)-2-Chloro-3-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-trimethylsilanyloxy-propionic acid ethyl ester | 138851-87-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (R)-2-Chloro-3-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-trimethylsilanyloxy-propionic acid ethyl ester
• CAS: 138851-87-3；138851-88-4
• 化学式: C₁₃H₂₅ClO₅Si
• 分子量: 324.877
• InChiKey: DFGNBFWJUBFQNG-GLYLRITDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.53
• 重原子数：
  20.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  53.99
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (R)-2-Chloro-3-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-trimethylsilanyloxy-propionic acid ethyl ester 在 乙醇锂 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以90%的产率得到(2S,3R)-3-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-oxirane-2-carboxylic acid ethyl ester
  参考文献：
  名称：

  Lanthanide(III) catalyzed aldol reactions of glyceraldehyde acetonide with ketene silyl acetals: Catalytic asymmetric route to monosaccharides

  摘要：

  The Pr-, Eu- and Ho(dppm)3 catalyzed aldol reactions of glyceraldehyde acetonide with ketene silyl acetals are described, where remarkably high anti-diastereofacial selection is achieved. Thus, the asymmetrc synthesis of 2-deoxy-D-ribonolactone and formal synthesis of 2-amino-2-deoxy-D-pentose by the lanthanide(III) catalyzed aldol reaction with ketene silyl acetals of acetate and alpha-chloroacetate, respectively are described.

  DOI：

  10.1016/s0957-4166(00)86145-5
• 作为产物：
  描述：

  [(2-Chloro-1-ethoxyethenyl)oxy](trimethyl)silane 、 (R)-(+)-2,2-二甲基-1,3-二氧戊环-4-甲醛 在 (-)-triseuropium(III) ((-)-Eu(dppm)3) 作用下， 以 二氯甲烷 为溶剂， 以100%的产率得到(R)-2-Chloro-3-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-trimethylsilanyloxy-propionic acid ethyl ester
  参考文献：
  名称：

  Lanthanide(III) catalyzed aldol reactions of glyceraldehyde acetonide with ketene silyl acetals: Catalytic asymmetric route to monosaccharides

  摘要：

  The Pr-, Eu- and Ho(dppm)3 catalyzed aldol reactions of glyceraldehyde acetonide with ketene silyl acetals are described, where remarkably high anti-diastereofacial selection is achieved. Thus, the asymmetrc synthesis of 2-deoxy-D-ribonolactone and formal synthesis of 2-amino-2-deoxy-D-pentose by the lanthanide(III) catalyzed aldol reaction with ketene silyl acetals of acetate and alpha-chloroacetate, respectively are described.

  DOI：

  10.1016/s0957-4166(00)86145-5