(2S)-1-[(Triphenylsilyl)oxy]propan-2-ol | 188524-93-8

• 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: (2S)-1-[(Triphenylsilyl)oxy]propan-2-ol
• 英文别名: (2S)-1-triphenylsilyloxypropan-2-ol
• CAS: 188524-93-8
• 化学式: C₂₁H₂₂O₂Si
• 分子量: 334.49
• InChiKey: ZWIUAQXBOJMKAV-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.05
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-乙酰氧基-2-氮杂环丁酮 、 (2S)-1-[(Triphenylsilyl)oxy]propan-2-ol 在 palladium diacetate 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 24.0h， 生成
  参考文献：
  名称：

  Strategies for the Formation of 1-Dethia-1-oxa-cephams

  摘要：

  The paper describes three possible routes for the formation of 1-dethia-1-oxa-cephams. The first two routes: (a) [2+2]cycloaddition to chiral vinyl ethers and (b) condensation of 4-acetoxyazetidin-2-one to chiral alcohols, are followed by the ring closure step involving N-alkylation. The third route (c) consists of N-alkylation prior to the cyclization step. In order to compare routes (a), (b) and (c), diastereomeric 1-dethia-3-(4-methoxybenzyloxy)-1-oxacephams were synthesized using three possible strategies. While the comparison of stereoselectivities of the [2+2]cycloaddition method (a) and the condensation (b) shows unequivocally the advantage of the former, the route (c) leads to the reverse direction of asymmetric induction relative to the first two steps and offers the highest asymmetric induction. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00405-1
• 作为产物：
  描述：

  L-乳酸甲酯 、 alkaline earth salt of/the/ methylsulfuric acid 生成 (2S)-1-[(Triphenylsilyl)oxy]propan-2-ol
  参考文献：
  名称：

  一种从羟基酸中提取石蜡和1-氧炔的方法。

  摘要：

  [2 + 2]氯磺酰基异氰酸酯与在醚的烷基部分带有立体中心的手性烷基乙烯基醚的环加成反应可提供相应的氮杂环丁烷-2-酮，在某些情况下具有相对较好的不对称诱导作用。已显示反应取决于立体中心的配体的空间要求。使立体化学结果合理化的模型基于乙烯基醚的s-顺式构象，其中最大的配体位于双键的平面内，而下一个最苛刻的取代基则被放置在双键上。

  DOI：

  10.1021/jo961683x

文献信息

• An Approach to Clavams and 1-Oxacephams from Hydroxy Acids
  作者：Bartłomiej Furman、Zbigniew Kałuża、Marek Chmielewski

  DOI：10.1021/jo961683x

  日期：1997.5.1

  [2 + 2] Cycloaddition of chlorosulfonyl isocyanate to chiral alkyl vinyl ethers bearing a sterogenic center in the alkyl part of the ether afford the corresponding azetidin-2-ones with relatively good asymmetric induction in certain cases. Reactions were shown to depend on steric requirements of the ligands at the stereogenic center. The model that rationalizes the stereochemical outcome is based on

  [2 + 2]氯磺酰基异氰酸酯与在醚的烷基部分带有立体中心的手性烷基乙烯基醚的环加成反应可提供相应的氮杂环丁烷-2-酮，在某些情况下具有相对较好的不对称诱导作用。已显示反应取决于立体中心的配体的空间要求。使立体化学结果合理化的模型基于乙烯基醚的s-顺式构象，其中最大的配体位于双键的平面内，而下一个最苛刻的取代基则被放置在双键上。
• Strategies for the Formation of 1-Dethia-1-oxa-cephams
  作者：Z Kałuża、B Furman、P Krajewski、M Chmielewski

  DOI：10.1016/s0040-4020(00)00405-1

  日期：2000.7

  The paper describes three possible routes for the formation of 1-dethia-1-oxa-cephams. The first two routes: (a) [2+2]cycloaddition to chiral vinyl ethers and (b) condensation of 4-acetoxyazetidin-2-one to chiral alcohols, are followed by the ring closure step involving N-alkylation. The third route (c) consists of N-alkylation prior to the cyclization step. In order to compare routes (a), (b) and (c), diastereomeric 1-dethia-3-(4-methoxybenzyloxy)-1-oxacephams were synthesized using three possible strategies. While the comparison of stereoselectivities of the [2+2]cycloaddition method (a) and the condensation (b) shows unequivocally the advantage of the former, the route (c) leads to the reverse direction of asymmetric induction relative to the first two steps and offers the highest asymmetric induction. (C) 2000 Elsevier Science Ltd. All rights reserved.