(2R,3R)-3-tert-Butoxycarbonylamino-5-(tert-butyl-diphenyl-silanyloxy)-2-ethyl-pentanoic acid | 175656-28-7

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (2R,3R)-3-tert-Butoxycarbonylamino-5-(tert-butyl-diphenyl-silanyloxy)-2-ethyl-pentanoic acid
• 英文别名: (2R,3R)-5-[tert-butyl(diphenyl)silyl]oxy-2-ethyl-3-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoic acid
• CAS: 175656-28-7
• 化学式: C₂₈H₄₁NO₅Si
• 分子量: 499.723
• InChiKey: DENRMIZIFONJNZ-DNQXCXABSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.96
• 重原子数：
  35
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,3R)-3-tert-Butoxycarbonylamino-5-(tert-butyl-diphenyl-silanyloxy)-2-ethyl-pentanoic acid 在 水 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 乙腈 、 三氟乙酸 为溶剂， 反应 5.33h， 生成 (3R,4R)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-3-ethyl-azetidin-2-one
  参考文献：
  名称：

  Formal Total Syntheses of the β-Lactam Antibiotics Thienamycin and PS-5

  摘要：

  Chiral nonracemic acetylenic acids of general structure 11, prepared using the Schreiber modification of the Nicholas reaction, have been converted to beta-amino acid derivatives of type 12 by a two-step sequence involving Curtius rearrangement followed by oxidative cleavage of the acetylenic bond. Amino acid derivatives 12 are excellent precursors for beta-lactams of the carbapenem class, including the important antibiotics thienamycin (1) and PS-5 (4).

  DOI：

  10.1021/jo952092u
• 作为产物：
  描述：

  {(1R,2S)-1-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2-ethyl-but-3-ynyl}-carbamic acid tert-butyl ester 在 氢氧化钾 、 potassium permanganate 、 sodium periodate 、 碳酸氢钠 作用下， 生成 (2R,3R)-3-tert-Butoxycarbonylamino-5-(tert-butyl-diphenyl-silanyloxy)-2-ethyl-pentanoic acid
  参考文献：
  名称：

  Formal Total Syntheses of the β-Lactam Antibiotics Thienamycin and PS-5

  摘要：

  Chiral nonracemic acetylenic acids of general structure 11, prepared using the Schreiber modification of the Nicholas reaction, have been converted to beta-amino acid derivatives of type 12 by a two-step sequence involving Curtius rearrangement followed by oxidative cleavage of the acetylenic bond. Amino acid derivatives 12 are excellent precursors for beta-lactams of the carbapenem class, including the important antibiotics thienamycin (1) and PS-5 (4).

  DOI：

  10.1021/jo952092u

文献信息

• Formal Total Syntheses of the β-Lactam Antibiotics Thienamycin and PS-5
  作者：Peter A. Jacobi、Shaun Murphree、Frederic Rupprecht、Wanjun Zheng

  DOI：10.1021/jo952092u

  日期：1996.1.1

  Chiral nonracemic acetylenic acids of general structure 11, prepared using the Schreiber modification of the Nicholas reaction, have been converted to beta-amino acid derivatives of type 12 by a two-step sequence involving Curtius rearrangement followed by oxidative cleavage of the acetylenic bond. Amino acid derivatives 12 are excellent precursors for beta-lactams of the carbapenem class, including the important antibiotics thienamycin (1) and PS-5 (4).