{[(R)-2-tert-Butoxycarbonylamino-3-(4-methoxy-benzylsulfanyl)-propyl]-[2-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-acetyl]-amino}-acetic acid ethyl ester | 887628-09-3

• 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: {[(R)-2-tert-Butoxycarbonylamino-3-(4-methoxy-benzylsulfanyl)-propyl]-[2-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-acetyl]-amino}-acetic acid ethyl ester
• CAS: 887628-09-3
• 化学式: C₂₇H₃₈N₄O₈S
• 分子量: 578.687
• InChiKey: VHJPSXGRKGLHNE-HXUWFJFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.07
• 重原子数：
  40.0
• 可旋转键数：
  13.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  149.03
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  {[(R)-2-tert-Butoxycarbonylamino-3-(4-methoxy-benzylsulfanyl)-propyl]-[2-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-acetyl]-amino}-acetic acid ethyl ester 在 lithium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 0.25h， 生成 N-[2-(2-{((R)-2-Acetylamino-3-mercapto-propyl)-[2-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-acetyl]-amino}-acetylamino)-ethyl]-N-carbamoylmethyl-2-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-acetamide
  参考文献：
  名称：

  Synthesis of thiol-modified peptide nucleic acids designed for post-assembly conjugation reactions

  摘要：

  Two orthogonally protected PNA monomers were prepared having the mercaptomethyl moiety attached to the PNA backbone. These building blocks were employed in solid-phase PNA synthesis and it was shown that Boc/S-p-methoxybenzyl protection scheme was only satisfactory for the introduction of N-terminal thiol modification while the Fmoc/S-butylthio protected monomer proved to be amenable to elongation. The mercaptomethyl modification did not influence the thermal stability of a PNA/RNA duplex. The feasibility of PNA-PNA native ligation was demonstrated. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.01.065
• 作为产物：
  描述：

  [(R)-2-(4-Methoxy-benzylsulfanyl)-1-(methoxy-methyl-carbamoyl)-ethyl]-carbamic acid tert-butyl ester 在 lithium aluminium tetrahydride 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三甲基膦 作用下， 以 四氢呋喃 、 乙醚 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 50.83h， 生成 {[(R)-2-tert-Butoxycarbonylamino-3-(4-methoxy-benzylsulfanyl)-propyl]-[2-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-acetyl]-amino}-acetic acid ethyl ester
  参考文献：
  名称：

  Synthesis of thiol-modified peptide nucleic acids designed for post-assembly conjugation reactions

  摘要：

  Two orthogonally protected PNA monomers were prepared having the mercaptomethyl moiety attached to the PNA backbone. These building blocks were employed in solid-phase PNA synthesis and it was shown that Boc/S-p-methoxybenzyl protection scheme was only satisfactory for the introduction of N-terminal thiol modification while the Fmoc/S-butylthio protected monomer proved to be amenable to elongation. The mercaptomethyl modification did not influence the thermal stability of a PNA/RNA duplex. The feasibility of PNA-PNA native ligation was demonstrated. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.01.065