(S)-1,1-dimethylethyl 2-<<4-(benzoylamino)-1,2-dihydro-2-oxo-1-pyrimidinyl>methyl>-6-oxo-1-piperidinecarboxylate | 135697-17-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (S)-1,1-dimethylethyl 2-<<4-(benzoylamino)-1,2-dihydro-2-oxo-1-pyrimidinyl>methyl>-6-oxo-1-piperidinecarboxylate
• 英文别名: tert-butyl (2S)-2-[(4-benzamido-2-oxopyrimidin-1-yl)methyl]-6-oxopiperidine-1-carboxylate
• CAS: 135697-17-5
• 化学式: C₂₂H₂₆N₄O₅
• 分子量: 426.472
• InChiKey: OFGAFLOMTNVPTE-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.81
• 重原子数：
  31.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  110.6
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (S)-1,1-dimethylethyl 2-<<4-(benzoylamino)-1,2-dihydro-2-oxo-1-pyrimidinyl>methyl>-6-oxo-1-piperidinecarboxylate 在 lithium hydroxide 作用下， 反应 0.67h， 以64%的产率得到(S)-δ-<<(1,1-dimethylethoxy)carbonyl>amino>-4-(benzoylamino)-1,2-dihydro-2-oxo-1-pyrimidinehexanoic acid
  参考文献：
  名称：

  Acyclic nucleic acid analogs: synthesis and oligomerization of .gamma.,4-diamino-2-oxo-1(2H)-pyrimidinepentanoic acid and .delta.,4-diamino-2-oxo-1(2H)-pyrimidinehexanoic acid

  摘要：

  Alkylation of the tosylates of N-t-Boc-5-(hydroxymethyl)-2-pyrrolidinone and N-t-Boc-6-(hydroxymethyl)-2-piperidinone with the sodium salt of cytosine in dimethyl sulfoxide, followed by acylation of the base exocyclic amine and selective opening of the lactam ring by alkaline hydrolysis, gave the title compounds, respectively, in protected form. Oligomerization was achieved by activation of the carboxyl group as the p-nitrophenyl ester and coupling with the free amine of another subunit in dimethylformamide or dimethyl sulfoxide. A hexamer of the pentanoic acid system could be easily prepared by stepwise coupling of the monomeric units or by block synthesis via trimers. The hexanoic acid derived hexamer could only be prepared by stepwise elongation, mostly due to problems of solubility for this backbone.

  DOI：

  10.1021/jo00021a010
• 作为产物：
  描述：

  (S)-1,1-dimethylethyl 2-<(4-methylbenzenesulfonyl)oxy)methyl>-6-oxo-1-piperidinecarboxylate 在 吡啶 、 potassium tert-butylate 作用下， 以 二甲基亚砜 为溶剂， 反应 8.0h， 生成 (S)-1,1-dimethylethyl 2-<<4-(benzoylamino)-1,2-dihydro-2-oxo-1-pyrimidinyl>methyl>-6-oxo-1-piperidinecarboxylate
  参考文献：
  名称：

  Acyclic nucleic acid analogs: synthesis and oligomerization of .gamma.,4-diamino-2-oxo-1(2H)-pyrimidinepentanoic acid and .delta.,4-diamino-2-oxo-1(2H)-pyrimidinehexanoic acid

  摘要：

  Alkylation of the tosylates of N-t-Boc-5-(hydroxymethyl)-2-pyrrolidinone and N-t-Boc-6-(hydroxymethyl)-2-piperidinone with the sodium salt of cytosine in dimethyl sulfoxide, followed by acylation of the base exocyclic amine and selective opening of the lactam ring by alkaline hydrolysis, gave the title compounds, respectively, in protected form. Oligomerization was achieved by activation of the carboxyl group as the p-nitrophenyl ester and coupling with the free amine of another subunit in dimethylformamide or dimethyl sulfoxide. A hexamer of the pentanoic acid system could be easily prepared by stepwise coupling of the monomeric units or by block synthesis via trimers. The hexanoic acid derived hexamer could only be prepared by stepwise elongation, mostly due to problems of solubility for this backbone.

  DOI：

  10.1021/jo00021a010

文献信息

• Acyclic nucleic acid analogs: synthesis and oligomerization of .gamma.,4-diamino-2-oxo-1(2H)-pyrimidinepentanoic acid and .delta.,4-diamino-2-oxo-1(2H)-pyrimidinehexanoic acid
  作者：Sung Ben Huang、Jeffrey S. Nelson、Dwight D. Weller

  DOI：10.1021/jo00021a010

  日期：1991.10

  Alkylation of the tosylates of N-t-Boc-5-(hydroxymethyl)-2-pyrrolidinone and N-t-Boc-6-(hydroxymethyl)-2-piperidinone with the sodium salt of cytosine in dimethyl sulfoxide, followed by acylation of the base exocyclic amine and selective opening of the lactam ring by alkaline hydrolysis, gave the title compounds, respectively, in protected form. Oligomerization was achieved by activation of the carboxyl group as the p-nitrophenyl ester and coupling with the free amine of another subunit in dimethylformamide or dimethyl sulfoxide. A hexamer of the pentanoic acid system could be easily prepared by stepwise coupling of the monomeric units or by block synthesis via trimers. The hexanoic acid derived hexamer could only be prepared by stepwise elongation, mostly due to problems of solubility for this backbone.