[(S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-tritylsulfanyl-propyl]-carbamic acid tert-butyl ester | 167015-78-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: [(S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-tritylsulfanyl-propyl]-carbamic acid tert-butyl ester
• CAS: 167015-78-3
• 化学式: C₄₂H₄₂N₂O₄S
• 分子量: 670.872
• InChiKey: JJQDWLFYGWIGPH-XIFFEERXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.14
• 重原子数：
  49.0
• 可旋转键数：
  11.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  76.66
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  [(S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-tritylsulfanyl-propyl]-carbamic acid tert-butyl ester 在 吡啶 、 碘 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 [(S)-3-tert-Butyldisulfanyl-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propyl]-[2-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-acetyl]-carbamic acid tert-butyl 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
• 作为产物：
  描述：

  9H-fluoren-9-ylmethyl N-[(2S)-1-[methoxy(methyl)amino]-1-oxo-3-tritylsulfanylpropan-2-yl]carbamate 在 lithium aluminium tetrahydride 、 3 A molecular sieve 、 sodium cyanoborohydride 作用下， 以 甲醇 、 乙醚 为溶剂， 生成 [(S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-tritylsulfanyl-propyl]-carbamic acid tert-butyl 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