(3R,4S)-4-[(E)-2-iodoprop-1-enyl]-1-[(2S)-2-[(4-methoxyphenyl)methoxy]propanoyl]-3-methylazetidin-2-one | 332837-95-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: (3R,4S)-4-[(E)-2-iodoprop-1-enyl]-1-[(2S)-2-[(4-methoxyphenyl)methoxy]propanoyl]-3-methylazetidin-2-one
• CAS: 332837-95-3
• 化学式: C₁₈H₂₂INO₄
• 分子量: 443.281
• InChiKey: USYZLVNKFSIIEX-PVYAWXLGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  甲醇 、 (3R,4S)-4-[(E)-2-iodoprop-1-enyl]-1-[(2S)-2-[(4-methoxyphenyl)methoxy]propanoyl]-3-methylazetidin-2-one 在 potassium cyanide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以88%的产率得到
  参考文献：
  名称：

  An approach to the total synthesis of lankacidins: synthesis of advanced macrocyclic precursors

  摘要：

  The macrocyclic tetraenes 11 and 19, possible precursors of lankacidin C 1, have been prepared using intramolecular Stille reactions to close the macrocyclic rings. The Stille precursor 10 was prepared by stereoselective acylation of the azetidinone 3 using the thioester 7. After reduction and deprotection, cyclisation gave the macrocyclic product 11 in 55% yield. Alternatively, the Boc-protected amino-ester 17 was prepared by ring-opening of the azetidinone, and cyclised to the macrocycle 19 in 48% yield. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)02261-9
• 作为产物：
  描述：

  2,2,2-三氯代亚氨逐乙酸-4-甲氧基苄酯 在 4-二甲氨基吡啶 、 草酰氯 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (3R,4S)-4-[(E)-2-iodoprop-1-enyl]-1-[(2S)-2-[(4-methoxyphenyl)methoxy]propanoyl]-3-methylazetidin-2-one
  参考文献：
  名称：

  An approach to the total synthesis of lankacidins: synthesis of advanced macrocyclic precursors

  摘要：

  The macrocyclic tetraenes 11 and 19, possible precursors of lankacidin C 1, have been prepared using intramolecular Stille reactions to close the macrocyclic rings. The Stille precursor 10 was prepared by stereoselective acylation of the azetidinone 3 using the thioester 7. After reduction and deprotection, cyclisation gave the macrocyclic product 11 in 55% yield. Alternatively, the Boc-protected amino-ester 17 was prepared by ring-opening of the azetidinone, and cyclised to the macrocycle 19 in 48% yield. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)02261-9