(3R,4R)-3-benzyl-1-[bis(trimethylsilyl)methyl]-4-methyl-3-[(4S,5R)-4,5-diphenyl-2-oxo-oxazolidin-3-yl]-azetidin-2-one | 813440-34-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (3R,4R)-3-benzyl-1-[bis(trimethylsilyl)methyl]-4-methyl-3-[(4S,5R)-4,5-diphenyl-2-oxo-oxazolidin-3-yl]-azetidin-2-one
• 英文别名: (4S,5R)-3-[(2R,3R)-3-benzyl-1-[bis(trimethylsilyl)methyl]-2-methyl-4-oxoazetidin-3-yl]-4,5-diphenyl-1,3-oxazolidin-2-one
• CAS: 813440-34-5
• 化学式: C₃₃H₄₂N₂O₃Si₂
• 分子量: 570.879
• InChiKey: BRUDLAPQVWNAOF-SKWRWUNHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.26
• 重原子数：
  40
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  49.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3R,4R)-3-benzyl-1-[bis(trimethylsilyl)methyl]-4-methyl-3-[(4S,5R)-4,5-diphenyl-2-oxo-oxazolidin-3-yl]-azetidin-2-one 在 palladium dihydroxide ammonium cerium(IV) nitrate 、 氢气 、 caesium carbonate 作用下， 以 乙醇 、 乙腈 为溶剂， 60.0~80.0 ℃ 、1.1 MPa 条件下， 反应 24.0h， 生成 (3-benzyl-3-tert-butoxycarbonylamino-2-methyl-4-oxo-azetidin-1-yl)-acetic acid methyl ester
  参考文献：
  名称：

  Synthesis of Type II β-Turn Surrogate Dipeptides Based on syn-α-Amino-α,β-dialkyl-β-lactams

  摘要：

  The achiral bis(trimethylsilyl)methyl group acts as an efficient stereochemical determinant of the alpha-alkylation reaction in beta-branched alpha-phenyloxazolidinyl- or alpha-diphenyloxazolidinyl-beta-lactams and provides the first stereocontrolled access to syn-alpha-amino-alpha,beta-dialkyl(aryl)-beta-lactams. These products are readily transformed into type II beta-turn mimetic surrogates 2B.

  DOI：

  10.1021/ol048348c
• 作为产物：
  描述：

  溴甲苯 、 (3S,4R)-1-[bis(trimethylsilyl)methyl]-4-methyl-3-[(4S,5R)-4,5-diphenyl-2-oxo-oxazolidin-3-yl]-azetidin-2-one 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 0.17h， 以67%的产率得到(3R,4R)-3-benzyl-1-[bis(trimethylsilyl)methyl]-4-methyl-3-[(4S,5R)-4,5-diphenyl-2-oxo-oxazolidin-3-yl]-azetidin-2-one
  参考文献：
  名称：

  Synthesis of Type II β-Turn Surrogate Dipeptides Based on syn-α-Amino-α,β-dialkyl-β-lactams

  摘要：

  The achiral bis(trimethylsilyl)methyl group acts as an efficient stereochemical determinant of the alpha-alkylation reaction in beta-branched alpha-phenyloxazolidinyl- or alpha-diphenyloxazolidinyl-beta-lactams and provides the first stereocontrolled access to syn-alpha-amino-alpha,beta-dialkyl(aryl)-beta-lactams. These products are readily transformed into type II beta-turn mimetic surrogates 2B.

  DOI：

  10.1021/ol048348c

文献信息

• Synthesis of Type II β-Turn Surrogate Dipeptides Based on <i>s</i><i>yn</i>-α-Amino-α,β-dialkyl-β-lactams
  作者：Claudio Palomo、Jesus M. Aizpurua、Iñaki Ganboa、Ana Benito、Lourdes Cuerdo、Raluca M. Fratila、Azucena Jimenez、Iraida Loinaz、José I. Miranda、Kinga R. Pytlewska、Andreea Micle、Anthony Linden

  DOI：10.1021/ol048348c

  日期：2004.11.1

  The achiral bis(trimethylsilyl)methyl group acts as an efficient stereochemical determinant of the alpha-alkylation reaction in beta-branched alpha-phenyloxazolidinyl- or alpha-diphenyloxazolidinyl-beta-lactams and provides the first stereocontrolled access to syn-alpha-amino-alpha,beta-dialkyl(aryl)-beta-lactams. These products are readily transformed into type II beta-turn mimetic surrogates 2B.