3-[(2S,3S)-3-((R)-1-Benzyloxy-ethyl)-2-methyl-5-trimethylsilanyl-pent-4-ynoyl]-oxazolidin-2-one | 149885-03-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-[(2S,3S)-3-((R)-1-Benzyloxy-ethyl)-2-methyl-5-trimethylsilanyl-pent-4-ynoyl]-oxazolidin-2-one
• 英文别名: 3-[(2S,3S)-2-methyl-3-[(1R)-1-phenylmethoxyethyl]-5-trimethylsilylpent-4-ynoyl]-1,3-oxazolidin-2-one
• CAS: 149885-03-0
• 化学式: C₂₁H₂₉NO₄Si
• 分子量: 387.551
• InChiKey: CPVKIRKTVOAMNH-YQVWRLOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 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：

  3-[(2S,3S)-3-((R)-1-Benzyloxy-ethyl)-2-methyl-5-trimethylsilanyl-pent-4-ynoyl]-oxazolidin-2-one 在 lithium hydroxide 、 三甲基氯硅烷 、 二苯基磷酸 、 双氧水 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 苯 为溶剂， 反应 37.5h， 生成 [(1S,2R)-2-((R)-1-Benzyloxy-ethyl)-1-methyl-but-3-ynyl]-carbamic acid tert-butyl ester
  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：

  、 4(R)-benzyloxy-3-methoxy-1-(trimethylsilyl)pentyne, hexacarbonyldicobal complex 在 ammonium cerium(IV) nitrate 、 i-PrNEt 、 三氟甲磺酸二丁硼 作用下， 生成 3-[(2S,3S)-3-((R)-1-Benzyloxy-ethyl)-2-methyl-5-trimethylsilanyl-pent-4-ynoyl]-oxazolidin-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

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).