(4S,5R)-3-[(2R,3R)-3-((R)-1-Benzyloxy-ethyl)-2-methyl-5-trimethylsilanyl-pent-4-ynoyl]-4-methyl-5-phenyl-oxazolidin-2-one | 149836-94-2

• 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: (4S,5R)-3-[(2R,3R)-3-((R)-1-Benzyloxy-ethyl)-2-methyl-5-trimethylsilanyl-pent-4-ynoyl]-4-methyl-5-phenyl-oxazolidin-2-one
• CAS: 149836-94-2
• 化学式: C₂₈H₃₅NO₄Si
• 分子量: 477.676
• InChiKey: JWVRFMTYTFVXTJ-KWLALQDESA-N

物化性质

• 沸点：
  582.1±50.0 °C(predicted)
• 密度：
  1.097±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

反应信息

• 作为反应物：
  描述：

  (4S,5R)-3-[(2R,3R)-3-((R)-1-Benzyloxy-ethyl)-2-methyl-5-trimethylsilanyl-pent-4-ynoyl]-4-methyl-5-phenyl-oxazolidin-2-one 在 lithium hydroxide 、 双氧水 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 16.0h， 以39%的产率得到(2R,3R)-3-((R)-1-Benzyloxy-ethyl)-2-methyl-pent-4-ynoic 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
• 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 (4S,5R)-3-[(2R,3R)-3-((R)-1-Benzyloxy-ethyl)-2-methyl-5-trimethylsilanyl-pent-4-ynoyl]-4-methyl-5-phenyl-oxazolidin-2-one 、 (4S,5R)-3-[(2R,3S)-3-((R)-1-Benzyloxy-ethyl)-2-methyl-5-trimethylsilanyl-pent-4-ynoyl]-4-methyl-5-phenyl-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

• A versatile synthesis of β-amino acids using the nicholas reaction. II. Formal total synthesis of thienamycin.
  作者：Peter A. Jacobi、Wanjun Zheng

  DOI：10.1016/s0040-4039(00)77631-3

  日期：1993.4

  Homochiral acetylenic acid 26, prepared using the Schreiber modification of the Nicholas reaction, has been converted to β-amino acid derivative 28 by a two step sequence involving Curtius rearrangement fallowed by oxidative clevage of the acetylenic bond. Amino acid derivative 28 was then converted to thienamycin (β12) precursor 30 by cyclization with DCC followed by epmerization.

  使用尼古拉斯反应的施莱伯修饰法制备的手性炔酸26已经通过涉及炔键的氧化断裂而引起的库尔修斯重排的两步序列转化为β-氨基酸衍生物28。然后通过用DCC环化，然后进行异构化，将氨基酸衍生物28转化为噻吩霉素（β12）前体30。