methyl (2S,3S,4R)-4,5-(isopropylidenedioxy)-2-methyl-3-(trimethylsiloxy)pentanoate | 111998-48-2

• 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: methyl (2S,3S,4R)-4,5-(isopropylidenedioxy)-2-methyl-3-(trimethylsiloxy)pentanoate
• 英文别名: methyl (2R,3S,4R)-4,5-(isopropylidenedioxy)-2-methyl-3-(trimethylsiloxy)pentanoate
• CAS: 111998-48-2；111998-49-3；111998-50-6；111998-51-7；150521-25-8
• 化学式: C₁₃H₂₆O₅Si
• 分子量: 290.432
• InChiKey: BRTBNNRQXAEWJJ-HSOILSAZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.17
• 重原子数：
  19.0
• 可旋转键数：
  5.0
• 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：

  methyl (2S,3S,4R)-4,5-(isopropylidenedioxy)-2-methyl-3-(trimethylsiloxy)pentanoate 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 生成 1-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2-methyl-propane-1,3-diol
  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：

  [1-methoxyprop-1-enyloxy]trimethylsilane 、 (R)-(+)-2,2-二甲基-1,3-二氧戊环-4-甲醛 在 (+)-trispraseodymium(III) 作用下， 以 二氯甲烷 为溶剂， 生成 methyl (2S,3S,4R)-4,5-(isopropylidenedioxy)-2-methyl-3-(trimethylsiloxy)pentanoate
  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