(3R)-1-[bis(trimethylsilyl)-methyl]-3-tert-butoxycarbonylamino-3-isobutylazetidin-2-one | 910097-78-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: (3R)-1-[bis(trimethylsilyl)-methyl]-3-tert-butoxycarbonylamino-3-isobutylazetidin-2-one
• 英文别名: tert-butyl N-[(3R)-1-[bis(trimethylsilyl)methyl]-3-(2-methylpropyl)-2-oxoazetidin-3-yl]carbamate
• CAS: 910097-78-8
• 化学式: C₁₉H₄₀N₂O₃Si₂
• 分子量: 400.709
• InChiKey: GORRJJNFEWULGO-LJQANCHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.26
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  58.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3R)-1-[bis(trimethylsilyl)-methyl]-3-tert-butoxycarbonylamino-3-isobutylazetidin-2-one 在 四甲基乙二胺 、 仲丁基锂 、 氘代甲醇-d 作用下， 以 四氢呋喃 、 环己烷 为溶剂， 以67%的产率得到(3R)-3-benzyl-1-[bis(trimethylsilyl)-deutero-methyl]-3-(tert-butoxycarbonylamino)-3-isobutylazetidin-2-one
  参考文献：
  名称：

  Functionalization of N-[(Silyl)methyl]-β-lactam Carbanions with Carbon Electrophiles

  摘要：

  Latent acidity of alpha-alkyl-alpha-amino-N-[(silyl) methyl]-beta-lactams enabled a concise entry to lithium nonenolate N-methyl-azetidinone carbanions lithiated alpha' to the beta-lactam nitrogen, owing to the stabilizing "alpha-effect" of one or two trimethylsilyl groups. (BuLi)-Bu-n/TMEDA and 'BuLi/TMEDA were the bases of choice for complete deprotonation of di- and monosilylated beta-lactams, respectively. Trapping of the resulting carbanions with alkyl halides provided the corresponding N-[(alpha'-silyl)-alkyl]-beta-lactams, while carbon dioxide and related electrophiles such as benzyl chloroformates or isocyanates, afforded the corresponding silicon-free N-carboxymethyl-, N-benzyloxycarbonylmethyl-, and N-amidomethyl-beta-lactams in a single synthetic step. Likely structures of these unprecedented lithiated N-[(silyl) methyl]-beta-lactams were studied by MO calculations (B3LYP/6-31G*), and the origin of their relative stability was briefly discussed.

  DOI：

  10.1021/jo060537g
• 作为产物：
  描述：

  (3S)-1-[bis(trimethylsilyl)methyl]-3-[(4S)-4-phenyl-2-oxo-1,3-oxazolidin-3-yl]azetidin-2-one 在 氨 、 lithium 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 生成 (3R)-1-[bis(trimethylsilyl)-methyl]-3-tert-butoxycarbonylamino-3-isobutylazetidin-2-one
  参考文献：
  名称：

  α-Alkyl-α-Amino-β-Lactam Peptides: Design, Synthesis, and Conformational Features

  摘要：

  Remarkable asymmetric induction is achieved in the alkylation of the lithium enolate of the beta-lactam 1. This allows the first time access to a new family of peptidomimetics 2 with predictable conformational constraints.

  DOI：

  10.1002/(sici)1521-3773(19991018)38:20<3056::aid-anie3056>3.0.co;2-j