1-<(S)-1-(tert-butoxycarbonyl)ethyl>-(3R,4S)-3-azido-4-phenylazetidin-2-one | 78738-80-4

• 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: 1-<(S)-1-(tert-butoxycarbonyl)ethyl>-(3R,4S)-3-azido-4-phenylazetidin-2-one
• 英文别名: 1-(1(S)-t-butoxycarbonylethyl)-3(R)-azido-4(S)-phenylazetidin-2-one；tert-butyl (2S)-2-[(3R,4S)-3-azido-2-oxo-4-phenylazetidin-1-yl]propanoate
• CAS: 78738-80-4
• 化学式: C₁₆H₂₀N₄O₃
• 分子量: 316.36
• InChiKey: RUMRPYXZBAYTAS-UHTWSYAYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  61
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-<(S)-1-(tert-butoxycarbonyl)ethyl>-(3R,4S)-3-azido-4-phenylazetidin-2-one 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 生成 (S)-2-((3R,4S)-3-Amino-2-oxo-4-phenyl-azetidin-1-yl)-propionic acid tert-butyl ester
  参考文献：
  名称：

  通过叠氮基环丁二烯与带有手性β-内酰胺骨架的亚苄基胺的环加成反应，不对称合成双-β-内酰胺的有效方法

  摘要：

  在叠氮基酮与1-[（S -1-）-叔丁氧羰基乙基] -3-苄叉基氨基-4-苯基-氮杂环丁烷-2-酮的不对称环加成中观察到极高的立体选择性，这导致形成光学纯的双- β内酰胺。

  DOI：

  10.1039/c39810000344
• 作为产物：
  描述：

  L-丙氨酸叔丁酯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 1-<(S)-1-(tert-butoxycarbonyl)ethyl>-(3R,4S)-3-azido-4-phenylazetidin-2-one
  参考文献：
  名称：

  通过叠氮基环丁二烯与带有手性β-内酰胺骨架的亚苄基胺的环加成反应，不对称合成双-β-内酰胺的有效方法

  摘要：

  在叠氮基酮与1-[（S -1-）-叔丁氧羰基乙基] -3-苄叉基氨基-4-苯基-氮杂环丁烷-2-酮的不对称环加成中观察到极高的立体选择性，这导致形成光学纯的双- β内酰胺。

  DOI：

  10.1039/c39810000344

文献信息

• Effective method for the asymmetric synthesis of bis-β-lactams by the cycloaddition of azidoketen to benzylideneamines bearing a chiral β-lactam backbone
  作者：Naoto Hatanaka、Iwao Ojima

  DOI：10.1039/c39810000344

  日期：——

  Extremely high stereoselectivity was observed in the asymmetric cycloaddition of azidoketen to 1-[(S)-1-t-butoxycarbonylethyl]-3-benzylideneamino-4-phenyl-azetidin-2-ones, which gave rise to the formation of optically pure bis-β-lactams.

  在叠氮基酮与1-[（S -1-）-叔丁氧羰基乙基] -3-苄叉基氨基-4-苯基-氮杂环丁烷-2-酮的不对称环加成中观察到极高的立体选择性，这导致形成光学纯的双- β内酰胺。
• Process for the preparation of dipeptides
  申请人：Sagami Chemical Research Center

  公开号：US04352752A1

  公开（公告）日：1982-10-05

  There is provided a novel process for the preparation of a dipeptide represented by the formula: ##STR1## wherein Ar represents an aromatic group; R.sup.1 represents a hydrogen atom, an alkyl group or an aryl group; R.sup.2 represents a hydrogen atom, an alkyl group or an aromatic group; Y represents a hydroxy group, an amino group or an acylamino group, which comprises subjecting a .beta.-lactam compound represented by the formula: ##STR2## wherein Ar, R.sup.1 and R.sup.2 have the same meanings as defined above, and X represents a hydroxy group, an amino group or an acylamino group, an azido group or a benzyloxy group, to hydrogenolysis in the presence of a catalyst. The process can be practiced without any complicated procedure as seen in the conventional processes for the preparation of peptides.

  提供了一种新型的二肽制备方法，其化学式为：##STR1## 其中Ar代表芳香族基团; R.sup.1代表氢原子、烷基或芳基; R.sup.2代表氢原子、烷基或芳香族基团; Y代表羟基、氨基或酰胺基，其包括将一种β-内酰胺化合物置于催化剂存在下进行氢解反应，该化合物的化学式为：##STR2## 其中Ar、R.sup.1和R.sup.2与上述定义相同，X代表羟基、氨基或酰胺基、叠氮基或苄氧基。该方法可以不需要像传统的肽制备方法那样进行复杂的程序。
• Azetidines and bisazetidines. Their synthesis and use as the key intermediates to enantiomerically pure diamines, amino alcohols, and polyamines
  作者：Iwao Ojima、Mangzhu Zhao、Takehiko Yamato、Kazuaki Nakahashi、Mitsuo Yamashita、Rumiko Abe

  DOI：10.1021/jo00018a012

  日期：1991.8

  Highly selective reductions of beta-lactams (1, 5), direct-tandem bis-beta-lactams (6), and tandem bis-beta-lactams (7) to the corresponding azetidines (13, 14) and bisazetidines (11, 12) are successfully performed by using diisobutylaluminum hydride (DIBAL-H), monochlorohydroalane (AlH2Cl) and dichloroalane (AlHCl2) as specific reducing agents: Enantiomerically pure azetidines and bisazetidines are readily synthesized without loss of enantiomeric purity. Possible mechanisms that can accommodate the unique selectivity realized by hydroalanes are discussed. Hydrogenolysis of 2-arylazetidines and 2,2'-diarylbisazetidines on palladium catalyst or Raney-Ni gives the corresponding diamines, amino alcohols, polyamino alcohols, and polyamino ethers in excellent yields, which may serve as useful chiral chelating agents as well as chiral building blocks for organic synthesis and for chiral macrocycles.
• US4352752A
  申请人：——

  公开号：US4352752A

  公开（公告）日：1982-10-05
• Remarkable effects of lone pair-lone pair interactions on the extremely stereoselective [2 + 2] cycloaddition of azidoketene to chiral 3-imino-.beta.-lactams
  作者：Iwao Ojima、Kazuaki Nakahashi、Stephan M. Brandstadter、Naoto Hatanaka

  DOI：10.1021/ja00240a033

  日期：1987.3