(3S,4R)-4-(5-acetoxypent-3-ynyl)-3-[(R)-1-tert-butyldimethylsilyloxyethyl]-2-azetidinone | 362605-42-3

• 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: (3S,4R)-4-(5-acetoxypent-3-ynyl)-3-[(R)-1-tert-butyldimethylsilyloxyethyl]-2-azetidinone
• 英文别名: 5-[(2R,3S)-3-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-4-oxoazetidin-2-yl]pent-2-ynyl acetate
• CAS: 362605-42-3
• 化学式: C₁₈H₃₁NO₄Si
• 分子量: 353.534
• InChiKey: FLRVIGPOWKSLSF-FVQBIDKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.86
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3S,4R)-4-(5-acetoxypent-3-ynyl)-3-[(R)-1-tert-butyldimethylsilyloxyethyl]-2-azetidinone 在 tris(dibenzylideneacetone)dipalladium (0) caesium carbonate 、 三(邻甲基苯基)磷 作用下， 以 甲苯 为溶剂， 反应 4.0h， 以6%的产率得到(5R,6S)-6-[(R)-1-tert-butyldimethylsilyloxyethyl]-3-vinylidene-carbapenam
  参考文献：
  名称：

  Novel Synthesis of Carbapenam by Intramolecular Attack of Lactam Nitrogen toward η¹-Allenyl and η³-Propargylpalladium Complex

  摘要：

  When a THF solution of beta-lactam having propargyl phosphate was warmed in the presence of 5 mol % of Pd-2(dba)(3).CHCl3, 20 mol % of a bidentate ligand, and sodium acetate (1.5 equiv) at 40 degreesC for 22 h, carbapenam was produced in high yield. In this reaction, the lactam nitrogen attacked the central carbon of a eta(3)-propargylpalladium complex, which was formed from propargyl phosphate and Pd(0).

  DOI：

  10.1021/jo030123c
• 作为产物：
  描述：

  (3S,4R)-1-(tert-butyldimethylsilyl)-3-[(R)-1-tert-butyldimethylsilyloxyethyl]-4-(5-hydroxypent-3-ynyl)-2-azetidinone 在 吡啶 、 potassium fluoride 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 11.0h， 生成 (3S,4R)-4-(5-acetoxypent-3-ynyl)-3-[(R)-1-tert-butyldimethylsilyloxyethyl]-2-azetidinone
  参考文献：
  名称：

  Novel Synthesis of Carbapenam by Intramolecular Attack of Lactam Nitrogen toward η¹-Allenyl and η³-Propargylpalladium Complex

  摘要：

  When a THF solution of beta-lactam having propargyl phosphate was warmed in the presence of 5 mol % of Pd-2(dba)(3).CHCl3, 20 mol % of a bidentate ligand, and sodium acetate (1.5 equiv) at 40 degreesC for 22 h, carbapenam was produced in high yield. In this reaction, the lactam nitrogen attacked the central carbon of a eta(3)-propargylpalladium complex, which was formed from propargyl phosphate and Pd(0).

  DOI：

  10.1021/jo030123c

文献信息

• Construction of a carbapenam skeleton using palladium-catalyzed cyclization
  作者：Yuji Kozawa、Miwako Mori

  DOI：10.1016/s0040-4039(01)00870-x

  日期：2001.7

  When a THF solution of beta -lactam having propargyl phosphate was warmed in the presence of 5 mol of Pd-2(dba)(3). CHCl3, 20 mol% of bidentate ligand and sodium acetate (1.5 equiv.) at 40 degreesC for 22 h, carbapenam was produced in high yield. In this reaction, the lactam nitrogen attacked the central sp carbon of a sigma -allenylpalladium complex, which was formed from propargyl phosphate and Pd(0). (C) 2001 Elsevier Science Ltd. All rights reserved.