(R)-5-Benzyloxy-3-trimethylsilanyloxy-pentanal | 309755-03-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-5-Benzyloxy-3-trimethylsilanyloxy-pentanal
• 英文别名: (3R)-5-phenylmethoxy-3-trimethylsilyloxypentanal
• CAS: 309755-03-1
• 化学式: C₁₅H₂₄O₃Si
• 分子量: 280.439
• InChiKey: VTAJPIMHNXPBAG-HNNXBMFYSA-N

物化性质

• 沸点：
  345.5±42.0 °C(predicted)
• 密度：
  0.987±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-5-Benzyloxy-3-trimethylsilanyloxy-pentanal 在 potassium cyanide 、 18-冠醚-6 、 DL-10-camphorsulfonic acid 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醚 、 水 、 丙酮 为溶剂， 反应 44.42h， 生成 (4S,6R)-4-cyano-4-(2-(tert-butyldimethylsilyloxy)-ethyl)-6-benzyloxyethyl-2,2-dimethyl-1,3-dioxane
  参考文献：
  名称：

  Empirical Model for the Molar Rotations of syn-2,2-Dimethyl-1,3-dioxanes

  摘要：

  [GRAPHICS]A useful method for the prediction of molar rotation ([Phi]) of syn-2,2-dimethyl-1,3-dioxanes (acetonides) is described. A series of acetonides were prepared by standard methods. A simple additive relationship between the substituents (R, R') and molar rotation was realized.

  DOI：

  10.1021/ol0263550
• 作为产物：
  描述：

  3-苄氧基丙醛 在 2,6-二甲基吡啶 、 N-(p-toluenesulfonyl)-L-valine 、 偶氮二异丁腈 、 (S)-oxazaborolidinone derived from BH₃*THF 、 三正丁基氢锡 、 二异丁基氢化铝 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 生成 (R)-5-Benzyloxy-3-trimethylsilanyloxy-pentanal
  参考文献：
  名称：

  An effective extension of the polyacetate chain in the polyene macrolide antibiotic filipin III, based on chiral oxazaborolidinone-promoted asymmetric aldol reactions

  摘要：

  The enantioselective construction of the iterative polyacetate unit 3 in filipin III has been accomplished, essentially by an aldol strategy based on chiral oxazaborolidinone-promoted asymmetric aldol reactions. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01289-2

文献信息

• An effective extension of the polyacetate chain in the polyene macrolide antibiotic filipin III, based on chiral oxazaborolidinone-promoted asymmetric aldol reactions
  作者：Syun-ichi Kiyooka、Mostofa A Hena、Tomomi Yabukami、Kazunori Murai、Fumitaka Goto

  DOI：10.1016/s0040-4039(00)01289-2

  日期：2000.9

  The enantioselective construction of the iterative polyacetate unit 3 in filipin III has been accomplished, essentially by an aldol strategy based on chiral oxazaborolidinone-promoted asymmetric aldol reactions. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Empirical Model for the Molar Rotations of <i>syn</i>-2,2-Dimethyl-1,3-dioxanes
  作者：Christopher D. Anderson、Scott D. Rychnovsky

  DOI：10.1021/ol0263550

  日期：2002.9.1

  [GRAPHICS]A useful method for the prediction of molar rotation ([Phi]) of syn-2,2-dimethyl-1,3-dioxanes (acetonides) is described. A series of acetonides were prepared by standard methods. A simple additive relationship between the substituents (R, R') and molar rotation was realized.