(3R)-3-benzyl-3-tert-butoxycarbonylamino-1-carboxymethyl-azetidin-2-one | 254112-87-3

• 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)-3-benzyl-3-tert-butoxycarbonylamino-1-carboxymethyl-azetidin-2-one
• 英文别名: (3R)-3-benzyl-1-carboxymethyl-3-tert-butoxycarbonylaminoazetidin-2-one；2-[(3R)-3-benzyl-3-[(2-methylpropan-2-yl)oxycarbonylamino]-2-oxoazetidin-1-yl]acetic acid
• CAS: 254112-87-3
• 化学式: C₁₇H₂₂N₂O₅
• 分子量: 334.372
• InChiKey: SWBCOLIYKRGNFX-QGZVFWFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  95.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3R)-3-benzyl-3-tert-butoxycarbonylamino-1-carboxymethyl-azetidin-2-one 在 钯 1-甲基吡咯烷 、 吡啶 、 三聚氟氰 、 氢气 作用下， 生成 2-[2-((R)-3-Benzyl-3-tert-butoxycarbonylamino-2-oxo-azetidin-1-yl)-acetylamino]-2-methyl-propionic acid
  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
• 作为产物：
  描述：

  (3R)-3-benzyl-1-bis(trimethylsilyl)methyl-3-(tert-butoxycarbonylamino)azetidin-2-one 在 palladium on activated charcoal ammonium cerium(IV) nitrate 、 氢气 、 碳酸氢钠 、 caesium carbonate 作用下， 生成 (3R)-3-benzyl-3-tert-butoxycarbonylamino-1-carboxymethyl-azetidin-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

文献信息

• Development of a New Family of Conformationally Restricted Peptides as Potent Nucleators of β-Turns. Design, Synthesis, Structure, and Biological Evaluation of a β-Lactam Peptide Analogue of Melanostatin
  作者：Claudio Palomo、Jesus M. Aizpurua、Ana Benito、José Ignacio Miranda、Raluca M. Fratila、Carlos Matute、Maria Domercq、Federico Gago、Sonsoles Martin-Santamaria、Anthony Linden

  DOI：10.1021/ja038180a

  日期：2003.12.1

  annealing techniques, showing a strong tendency to form stable type II or type II' beta-turns either in the solid state or in highly coordinating DMSO solutions. Tetrapeptide models containing syn- or anti-alpha,beta-dialkyl-alpha-amino-beta-lactam rings have also been synthesized and their conformations analyzed, revealing that alpha-alkyl substitution is essential for beta-turn stabilization. A beta-lactam

  新型对映体纯 (i)-(β-内酰胺)-(Gly)-(i+3) 肽模型，定义为存在中心 α-烷基-α-氨基-β-内酰胺环，放置为 (i+1 ) 残基，通过合适的 N-[双(三甲基甲硅烷基)甲基]-β-内酰胺的α-烷基化以完全立体控制的方式合成。这些 β-内酰胺假肽的结构特性已经通过 X 射线晶体学、分子动力学模拟和 NOESY 抑制 NMR 模拟退火技术进行了研究，显示出形成稳定的 II 型或 II 型'β-转角的强烈趋势。固态或高度协调的 DMSO 溶液。还合成了含有顺式或反式 α,β-二烷基-α-氨基-β-内酰胺环的四肽模型并分析了它们的构象，揭示α-烷基取代对于β-转角稳定是必不可少的。还制备了黑色素抑制素的 β-内酰胺类似物（PLG 酰胺），在 DMSO-d6 溶液中表征为 II 型β-转角，并通过竞争性结合试验作为大鼠神经元培养细胞中的多巴胺能 D2 调节剂进行测试，显示出中等微摩
• Functionalization of <i>N</i>-[(Silyl)methyl]-β-lactam Carbanions with Carbon Electrophiles
  作者：Claudio Palomo、Jesus M. Aizpurua、Ana Benito、Lourdes Cuerdo、Raluca M. Fratila、José I. Miranda、Anthony Linden

  DOI：10.1021/jo060537g

  日期：2006.8.1

  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.
• α-Alkyl-α-Amino-β-Lactam Peptides: Design, Synthesis, and Conformational Features
  作者：Claudio Palomo、Jesus M. Aizpurua、Ana Benito、Regina Galarza、Uttam K. Khamrai、Jordi Vazquez、Beatriz de Pascual-Teresa、Pedro M. Nieto、Anthony Linden

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

  日期：1999.10.18

  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.