(2R,3R)-3-Amino-5-(tert-butyl-diphenyl-silanyloxy)-2-ethyl-pentanoic acid | 1026837-32-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2R,3R)-3-Amino-5-(tert-butyl-diphenyl-silanyloxy)-2-ethyl-pentanoic acid
• 英文别名: (2R,3R)-3-amino-5-[tert-butyl(diphenyl)silyl]oxy-2-ethylpentanoic acid
• CAS: 1026837-32-0
• 化学式: C₂₃H₃₃NO₃Si
• 分子量: 399.605
• InChiKey: BYXUDLAUVYKWGV-NHCUHLMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.39
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  72.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,3R)-3-Amino-5-(tert-butyl-diphenyl-silanyloxy)-2-ethyl-pentanoic acid 在 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 乙腈 为溶剂， 反应 5.0h， 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 、 水 、 碳酸氢钠 作用下， 以 三氟乙酸 为溶剂， 反应 5.83h， 生成 (2R,3R)-3-Amino-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).