[(3S)-1-azidohex-5-en-3-yl] tert-butyl carbonate | 1000206-08-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机碳酸及其衍生物
• 英文名称: [(3S)-1-azidohex-5-en-3-yl] tert-butyl carbonate
• CAS: 1000206-08-5
• 化学式: C₁₁H₁₉N₃O₃
• 分子量: 241.29
• InChiKey: SGHKCEOQDHZOJP-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  17
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  49.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [(3S)-1-azidohex-5-en-3-yl] tert-butyl carbonate 在 N-碘代丁二酰亚胺 作用下， 以 乙腈 为溶剂， 反应 20.0h， 以87%的产率得到(4R,6R)-4-(2-azidoethyl)-6-(iodomethyl)-1,3-dioxan-2-one
  参考文献：
  名称：

  An efficient organocatalytic route to the atorvastatin side-chain

  摘要：

  An organocatalytic route to the synthesis of the atorvastatin side-chain, a building block present in the statin family, is described using L-proline-catalyzed alpha-aminooxylation of an aldehyde. The method also employs an iodine-induced intramolecular electrophilic cyclization of a carbonate to produce the iodocarbonate in a highly diastereoselective manner. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.09.133
• 作为产物：
  描述：

  在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以83%的产率得到[(3S)-1-azidohex-5-en-3-yl] tert-butyl carbonate
  参考文献：
  名称：

  An efficient organocatalytic route to the atorvastatin side-chain

  摘要：

  An organocatalytic route to the synthesis of the atorvastatin side-chain, a building block present in the statin family, is described using L-proline-catalyzed alpha-aminooxylation of an aldehyde. The method also employs an iodine-induced intramolecular electrophilic cyclization of a carbonate to produce the iodocarbonate in a highly diastereoselective manner. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.09.133

文献信息

• An efficient organocatalytic route to the atorvastatin side-chain
  作者：Shyla George、Arumugam Sudalai

  DOI：10.1016/j.tetlet.2007.09.133

  日期：2007.11

  An organocatalytic route to the synthesis of the atorvastatin side-chain, a building block present in the statin family, is described using L-proline-catalyzed alpha-aminooxylation of an aldehyde. The method also employs an iodine-induced intramolecular electrophilic cyclization of a carbonate to produce the iodocarbonate in a highly diastereoselective manner. (C) 2007 Elsevier Ltd. All rights reserved.