(3R)-3-benzyl-1-tert-butoxycarbonyl-3-(tert-butoxycarbonylamino)azetidin-2-one | 301161-16-0

• 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-1-tert-butoxycarbonyl-3-(tert-butoxycarbonylamino)azetidin-2-one
• 英文别名: tert-butyl (3R)-3-benzyl-3-[(2-methylpropan-2-yl)oxycarbonylamino]-2-oxoazetidine-1-carboxylate
• CAS: 301161-16-0
• 化学式: C₂₀H₂₈N₂O₅
• 分子量: 376.453
• InChiKey: RWVAGNRKLOZXFW-HXUWFJFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  84.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S)-2-氨基-4-甲基戊酸甲酯 、 (3R)-3-benzyl-1-tert-butoxycarbonyl-3-(tert-butoxycarbonylamino)azetidin-2-one 在 potassium cyanide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 19.0h， 以75%的产率得到(2R)-2-benzyl-2,3-di-tert-butoxycarbonylamino-N-[L-Val-(OMe)]-propanamide
  参考文献：
  名称：

  On the Question of the Diastereoselective Alkylation of 4-Unsubstituted 3-Amino β-Lactams. A Concise Synthesis of α-Branched α-Amino β-Lactams and their Coupling with α-Amino Acid Esters

  摘要：

  The reaction of [(4S)-2-oxo-4-phenyloxazolidin-3-yl]acetic acid chloride with N-methylidene-bis-[(trimethylsilyl)methyl] amine and triethylamine in refluxing chloroform leads to a 4-unsubstituted beta-lactam able to undergo highly asymmetric alkylations at the alpha-position of the beta-lactam ring. The resulting adducts can be efficiently transformed into N-unsubstituted alpha-branched 3-amino beta-lactams as the cyclisized forms of alpha-branched beta-aminoalanines or transformed into their imide N-Boc derivatives, which are suitable substrates for non-proteinogenic peptide synthesis, by reaction with alpha-amino esters. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00406-3
• 作为产物：
  描述：

  (3R)-3-benzyl-1-bis(trimethylsilyl)methyl-3-(tert-butoxycarbonylamino)azetidin-2-one 在 4-二甲氨基吡啶 、 ammonium cerium(IV) nitrate 、 碳酸氢钠 、 sodium carbonate 作用下， 以 丙酮 、 乙腈 为溶剂， 反应 44.75h， 生成 (3R)-3-benzyl-1-tert-butoxycarbonyl-3-(tert-butoxycarbonylamino)azetidin-2-one
  参考文献：
  名称：

  On the Question of the Diastereoselective Alkylation of 4-Unsubstituted 3-Amino β-Lactams. A Concise Synthesis of α-Branched α-Amino β-Lactams and their Coupling with α-Amino Acid Esters

  摘要：

  The reaction of [(4S)-2-oxo-4-phenyloxazolidin-3-yl]acetic acid chloride with N-methylidene-bis-[(trimethylsilyl)methyl] amine and triethylamine in refluxing chloroform leads to a 4-unsubstituted beta-lactam able to undergo highly asymmetric alkylations at the alpha-position of the beta-lactam ring. The resulting adducts can be efficiently transformed into N-unsubstituted alpha-branched 3-amino beta-lactams as the cyclisized forms of alpha-branched beta-aminoalanines or transformed into their imide N-Boc derivatives, which are suitable substrates for non-proteinogenic peptide synthesis, by reaction with alpha-amino esters. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00406-3

文献信息

• On the Question of the Diastereoselective Alkylation of 4-Unsubstituted 3-Amino β-Lactams. A Concise Synthesis of α-Branched α-Amino β-Lactams and their Coupling with α-Amino Acid Esters
  作者：Claudio Palomo、Jesus M. Aizpurua、Regina Galarza、Ana Benito、Uttam K. Khamrai、Unni Eikeseth、Anthony Linden

  DOI：10.1016/s0040-4020(00)00406-3

  日期：2000.7

  The reaction of [(4S)-2-oxo-4-phenyloxazolidin-3-yl]acetic acid chloride with N-methylidene-bis-[(trimethylsilyl)methyl] amine and triethylamine in refluxing chloroform leads to a 4-unsubstituted beta-lactam able to undergo highly asymmetric alkylations at the alpha-position of the beta-lactam ring. The resulting adducts can be efficiently transformed into N-unsubstituted alpha-branched 3-amino beta-lactams as the cyclisized forms of alpha-branched beta-aminoalanines or transformed into their imide N-Boc derivatives, which are suitable substrates for non-proteinogenic peptide synthesis, by reaction with alpha-amino esters. (C) 2000 Elsevier Science Ltd. All rights reserved.