(S)-Benzo[1,3]dioxol-5-yl-(tert-butyl-dimethyl-silanyloxy)-((2S,3R)-2-methoxy-5-oxo-tetrahydro-furan-3-yl)-acetonitrile | 193466-49-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: (S)-Benzo[1,3]dioxol-5-yl-(tert-butyl-dimethyl-silanyloxy)-((2S,3R)-2-methoxy-5-oxo-tetrahydro-furan-3-yl)-acetonitrile
• CAS: 193466-49-8
• 化学式: C₂₀H₂₇NO₆Si
• 分子量: 405.523
• InChiKey: CQHHFXUKPCPDJV-ADLFWFRXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.69
• 重原子数：
  28.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  87.01
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (S)-Benzo[1,3]dioxol-5-yl-(tert-butyl-dimethyl-silanyloxy)-((2S,3R)-2-methoxy-5-oxo-tetrahydro-furan-3-yl)-acetonitrile 在 甲醇 、 sodium tetrahydroborate 作用下， 以 四氢呋喃 为溶剂， 以90%的产率得到(2S,3S)-2-Benzo[1,3]dioxol-5-yl-2-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-3-hydroxymethyl-pentanenitrile
  参考文献：
  名称：

  Asymmetric syntheses of lignans utilizing novel diastereoselective Michael addition of cyanohydrin: Syntheses of (+)-fargesin and (−)-picropodophyllone

  摘要：

  The Michael addition reaction of lithium salt of cyanohydrin to (S)- and (R)-3-(2,2-dimethyl-1,3-dioxolan-4-yl)-cis-2-propenoate (2 and 3) proceeded in 93% de in the presence of two equivalents of HMPA at -100 degrees C. This diastereoselectivity could be elucidated by the stereocontrol based on the 1,3-allylic strain. Utilizing this reaction, stereocontrolled syntheses of (+)-fargesin (6) and (-)-picropodophyllone (7) were achieved. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00643-1
• 作为产物：
  描述：

  Benzo[1,3]dioxol-5-yl-(tert-butyl-dimethyl-silanyloxy)-acetonitrile 在 六甲基磷酰三胺 、 sodium periodate 、 硫酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 24.5h， 生成 (S)-Benzo[1,3]dioxol-5-yl-(tert-butyl-dimethyl-silanyloxy)-((2S,3R)-2-methoxy-5-oxo-tetrahydro-furan-3-yl)-acetonitrile
  参考文献：
  名称：

  Asymmetric syntheses of lignans utilizing novel diastereoselective Michael addition of cyanohydrin: Syntheses of (+)-fargesin and (−)-picropodophyllone

  摘要：

  The Michael addition reaction of lithium salt of cyanohydrin to (S)- and (R)-3-(2,2-dimethyl-1,3-dioxolan-4-yl)-cis-2-propenoate (2 and 3) proceeded in 93% de in the presence of two equivalents of HMPA at -100 degrees C. This diastereoselectivity could be elucidated by the stereocontrol based on the 1,3-allylic strain. Utilizing this reaction, stereocontrolled syntheses of (+)-fargesin (6) and (-)-picropodophyllone (7) were achieved. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00643-1