(4S,5R)-3-[(3S,4R)-1-(Bis-trimethylsilanyl-methyl)-2-oxo-4-phenethyl-azetidin-3-yl]-4,5-diphenyl-oxazolidin-2-one | 198022-12-7

• 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: (4S,5R)-3-[(3S,4R)-1-(Bis-trimethylsilanyl-methyl)-2-oxo-4-phenethyl-azetidin-3-yl]-4,5-diphenyl-oxazolidin-2-one
• CAS: 198022-12-7
• 化学式: C₃₃H₄₂N₂O₃Si₂
• 分子量: 570.879
• InChiKey: DIOPAKPLYZKNBG-IBHPWDLASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.26
• 重原子数：
  40.0
• 可旋转键数：
  9.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  49.85
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  二碳酸二叔丁酯 、 (4S,5R)-3-[(3S,4R)-1-(Bis-trimethylsilanyl-methyl)-2-oxo-4-phenethyl-azetidin-3-yl]-4,5-diphenyl-oxazolidin-2-one 在 palladium dihydroxide 氢气 作用下， 以 乙醇 为溶剂， 反应 20.0h， 以80%的产率得到[(3S,4R)-1-(Bis-trimethylsilanyl-methyl)-2-oxo-4-phenethyl-azetidin-3-yl]-carbamic acid tert-butyl ester
  参考文献：
  名称：

  A Contribution to the Asymmetric Synthesis of 3-Amino β-Lactams: The Diastereoselective [2+2] Cycloaddition Reaction of Chiral Aminoketene Equivalents with Enolizable Aldehyde-Derived Imines

  摘要：

  AbstractN‐[Bis(trimethylsilyl)methyl]imines 9 show unique chemical properties when compared with conventional imines. Their reaction with optically pure aminoketenes derived from dehydrochlorination of 14 and 15 affords the corresponding 3‐amino‐4‐alkyl‐β‐lactams 16 and 17 in good yields and high diastereoselectivities. The mild deprotection of bis(trimethylsilyl)methyl‐ and phenyloxazolidinone moieties with, respectively, cerium(IV) ammonium nitrate and lithium/ammonia or hydrogen/Pd(OH)2 allows the preparation of a variety of β‐lactam antibiotic building blocks.

  DOI：

  10.1002/chem.19970030909
• 作为产物：
  描述：

  在 sodium hydroxide 、 草酰氯 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 氯仿 为溶剂， 反应 23.0h， 生成 (4S,5R)-3-[(3S,4R)-1-(Bis-trimethylsilanyl-methyl)-2-oxo-4-phenethyl-azetidin-3-yl]-4,5-diphenyl-oxazolidin-2-one
  参考文献：
  名称：

  A Contribution to the Asymmetric Synthesis of 3-Amino β-Lactams: The Diastereoselective [2+2] Cycloaddition Reaction of Chiral Aminoketene Equivalents with Enolizable Aldehyde-Derived Imines

  摘要：

  AbstractN‐[Bis(trimethylsilyl)methyl]imines 9 show unique chemical properties when compared with conventional imines. Their reaction with optically pure aminoketenes derived from dehydrochlorination of 14 and 15 affords the corresponding 3‐amino‐4‐alkyl‐β‐lactams 16 and 17 in good yields and high diastereoselectivities. The mild deprotection of bis(trimethylsilyl)methyl‐ and phenyloxazolidinone moieties with, respectively, cerium(IV) ammonium nitrate and lithium/ammonia or hydrogen/Pd(OH)2 allows the preparation of a variety of β‐lactam antibiotic building blocks.

  DOI：

  10.1002/chem.19970030909