phosphoric acid (S)-4-{(3S,4R)-3-[(R)-1-tert-butyldimethylsilyloxyethyl]-2-oxo-4-azetidinyl}pent-2-ynyl ester diethyl ester | 362605-39-8

• 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: phosphoric acid (S)-4-{(3S,4R)-3-[(R)-1-tert-butyldimethylsilyloxyethyl]-2-oxo-4-azetidinyl}pent-2-ynyl ester diethyl ester
• 英文别名: [(4S)-4-[(2R,3S)-3-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-4-oxoazetidin-2-yl]pent-2-ynyl] diethyl phosphate
• CAS: 362605-39-8
• 化学式: C₂₀H₃₈NO₆PSi
• 分子量: 447.584
• InChiKey: QVBPOYBAFLMUME-BSDSXHPESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.35
• 重原子数：
  29
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  83.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  sodium benzoate 、 phosphoric acid (S)-4-{(3S,4R)-3-[(R)-1-tert-butyldimethylsilyloxyethyl]-2-oxo-4-azetidinyl}pent-2-ynyl ester diethyl ester 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 1,1'-双(二苯基膦)二茂铁 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以60%的产率得到(1R,2R,5R,6S)-2-benzyloxy-6-[(R)-1-tert-butyldimethylsilyloxyethyl]-1-methyl-3-methylidene-carbapenam
  参考文献：
  名称：

  Construction of a carbapenam skeleton using palladium-catalyzed cyclization

  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 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.

  DOI：

  10.1016/s0040-4039(01)00870-x
• 作为产物：
  描述：

  (3S,4R)-1-(tert-butyldimethylsilyl)-3-[(R)-1-tert-butyldimethylsilyloxyethyl]-4-[4-hydroxy-(S)-1-methylbut-2-ynyl]-2-azetidinone 在 吡啶 、 4-二甲氨基吡啶 、 potassium fluoride 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 7.0h， 生成 phosphoric acid (S)-4-{(3S,4R)-3-[(R)-1-tert-butyldimethylsilyloxyethyl]-2-oxo-4-azetidinyl}pent-2-ynyl ester diethyl ester
  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

• Novel Synthesis of Carbapenam by Intramolecular Attack of Lactam Nitrogen toward η¹-Allenyl and η³-Propargylpalladium Complex
  作者：Yuji Kozawa、Miwako Mori

  DOI：10.1021/jo030123c

  日期：2003.10.1

  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).
• 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.