4-O-tert-butyldiphenylsilyl-2,3-di-O-isopropylidene-1(S)-(1-methyl-1-nitroethyl)-D-threitol | 1414957-17-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-O-tert-butyldiphenylsilyl-2,3-di-O-isopropylidene-1(S)-(1-methyl-1-nitroethyl)-D-threitol
• CAS: 1414957-17-7
• 化学式: C₂₆H₃₇NO₆Si
• 分子量: 487.668
• InChiKey: MUOBKUUZUAXTSV-XPWALMASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  34.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  91.06
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  2-溴2-硝基丙烷 、 (4R,5S)-trans-2,2-dimethyl-4-tert-butyldiphenylsiloxymethyl-5-formyl-1,3-dioxolane 在 indium 作用下， 以 四氢呋喃 为溶剂， 反应 4.33h， 以71%的产率得到4-O-tert-butyldiphenylsilyl-2,3-di-O-isopropylidene-1(S)-(1-methyl-1-nitroethyl)-D-threitol
  参考文献：
  名称：

  Synthesis of Sugar-Derived 2-Nitroalkanols via Henry Reaction Promoted by Samarium Diiodide or Indium

  摘要：

  We present herein an improved synthesis of nitro sugars, consisting of a Henry-type reaction of bromonitromethane and sugar aldehydes. The reaction can be promoted by either SmI2 or indium metal, yielding in both cases high yields and good diastereoisomeric ratios. However, while the SmI2-promoted reaction is very sensitive to steric factors and only gives satisfactory results with bromonitromethane, the indium-mediated reaction is not subjected to this limitation, giving excellent results with bromonitromethane as well as more hindered bromonitroalkanes.

  DOI：

  10.1055/s-0031-1290441