methyl (1'R,2R,3'S)-2-[2''-tert-butoxycarbonylamino-1''-[(thymin-1-yl)acetyl]aminoethyl]-4-(3'-acetyl-2',2'-dimethylcyclobutyl)butanoate | 917476-77-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl (1'R,2R,3'S)-2-[2''-tert-butoxycarbonylamino-1''-[(thymin-1-yl)acetyl]aminoethyl]-4-(3'-acetyl-2',2'-dimethylcyclobutyl)butanoate
• CAS: 917476-77-8
• 化学式: C₂₇H₄₂N₄O₈
• 分子量: 550.652
• InChiKey: HXNHZHYKNYAGJN-VAMGGRTRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.77
• 重原子数：
  39.0
• 可旋转键数：
  11.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  156.87
• 氢给体数：
  2.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  methyl (1'R,2R,3'S)-2-[2''-tert-butoxycarbonylamino-1''-[(thymin-1-yl)acetyl]aminoethyl]-4-(3'-acetyl-2',2'-dimethylcyclobutyl)butanoate 在 potassium carbonate 作用下， 以 甲醇 、 水 为溶剂， 反应 12.0h， 以24%的产率得到(1'R,2R,3'S)-2-[2''-tert-butoxycarbonylamino-1''-[(thymin-1-yl)acetyl]aminoethyl]-4-(3'-acetyl-2',2'-dimethylcyclobutyl)butanoic acid
  参考文献：
  名称：

  Cyclobutyl-carbonyl substituted PNA: synthesis and study of a novel PNA derivative

  摘要：

  A new, optically active, cyclobutyl-carbonyl substituted PNA monomer has been synthesized stereoselectively from a chiral amino acid prepared from (+)-alpha-pinene. A conformational search shows a lack of conformational bias for the monomer and incorporation of the monomer into a standard oligomer is tolerated without changing the binding affinity towards sequence complementary RNA, DNA or PNA targets. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.09.012
• 作为产物：
  描述：

  methyl (1'R,2R,3'S)-2-benzyloxycarbonylamino-4-(3'-acetyl-2',2'-dimethylcyclobutyl)butanoate 在 palladium on activated charcoal 氢气 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 20.0 ℃ 、506.62 kPa 条件下， 反应 6.67h， 生成 methyl (1'R,2R,3'S)-2-[2''-tert-butoxycarbonylamino-1''-[(thymin-1-yl)acetyl]aminoethyl]-4-(3'-acetyl-2',2'-dimethylcyclobutyl)butanoate
  参考文献：
  名称：

  Cyclobutyl-carbonyl substituted PNA: synthesis and study of a novel PNA derivative

  摘要：

  A new, optically active, cyclobutyl-carbonyl substituted PNA monomer has been synthesized stereoselectively from a chiral amino acid prepared from (+)-alpha-pinene. A conformational search shows a lack of conformational bias for the monomer and incorporation of the monomer into a standard oligomer is tolerated without changing the binding affinity towards sequence complementary RNA, DNA or PNA targets. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.09.012