甘氨酸,N-[2-[[(9H-芴-9-基甲氧基)羰基]氨基]乙基]-,苯甲酯,盐酸盐(1:1) | 511534-93-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 中文名称: 甘氨酸,N-[2-[[(9H-芴-9-基甲氧基)羰基]氨基]乙基]-,苯甲酯,盐酸盐(1:1)
• 英文名称: benzyl N-[2-((fluorenylmethoxycarbonyl)amino)ethyl]glycinate hydrochloride
• 英文别名: benzyl N-{2-[(9H-fluoren-9-yl)methoxycarbonyl]aminoethyl}glycinate hydrochloride；benzyl N-[2-(Fmoc)aminoethyl]glycinate；Glycine, N-[2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]ethyl]-, phenylmethyl ester, hydrochloride (1:1)；benzyl 2-[2-(9H-fluoren-9-ylmethoxycarbonylamino)ethylamino]acetate;hydrochloride
• CAS: 511534-93-3
• 化学式: C₂₆H₂₆N₂O₄*ClH
• 分子量: 466.964
• InChiKey: SDLXTUTWRJKAPN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.28
• 重原子数：
  33.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 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：

  甘氨酸,N-[2-[[(9H-芴-9-基甲氧基)羰基]氨基]乙基]-,苯甲酯,盐酸盐(1:1) 、 2-(2,6-双(双(叔丁氧羰基)氨基)-9H-嘌呤-9-基)乙酸 在 N,N-二异丙基乙胺 、 ((3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)oxy)tri(pyrrolidin-1-yl)phosphonium hexafluorophosphate(V) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.17h， 以94%的产率得到Benzyl 2-(N-(2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)ethyl)-2-(2,6-bis(bis(tert-butoxycarbonyl)amino)-9H-purin-9-yl)acetamido)acetate
  参考文献：
  名称：

  PNA monomers fully compatible with standard Fmoc-based solid-phase synthesis of pseudocomplementary PNA

  摘要：

  Here we report the synthesis of new PNA monomers for pseudocomplementary PNA (pcPNA) that are fully compatible with standard Fmoc chemistry. The thiocarbonyl group of the 2-thiouracil (sU) monomer was protected with the 4-methoxy-2-methybenzyl group (MMPM), while the exocyclic amino groups of diaminopurine (D) were protected with Boc groups. The newly synthesized monomers were incorporated into a 10-mer PNA oligomer using standard Fmoc chemistry for solid-phase synthesis. Oligomerization proceeded smoothly and the HPLC and MALDI-TOF MS analyses indicated that there was no remaining MMPM on the sU nucleobase. The new PNA monomers reported here would facilitate a wide range of applications, such as antigene PNAs and DNA nanotechnologies. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2017.06.015
• 作为产物：
  描述：

  tert-butyl N-[2-(N-9-fluorenylmethoxycarbonyl)aminoethyl]glycinate hydrochloride 、 苯甲醇 在 对甲苯磺酸 、 盐酸 作用下， 以 甲苯 、 水 、 乙酸乙酯 为溶剂， 反应 3.0h， 以96%的产率得到甘氨酸,N-[2-[[(9H-芴-9-基甲氧基)羰基]氨基]乙基]-,苯甲酯,盐酸盐(1:1)
  参考文献：
  名称：

  PNA monomers fully compatible with standard Fmoc-based solid-phase synthesis of pseudocomplementary PNA

  摘要：

  Here we report the synthesis of new PNA monomers for pseudocomplementary PNA (pcPNA) that are fully compatible with standard Fmoc chemistry. The thiocarbonyl group of the 2-thiouracil (sU) monomer was protected with the 4-methoxy-2-methybenzyl group (MMPM), while the exocyclic amino groups of diaminopurine (D) were protected with Boc groups. The newly synthesized monomers were incorporated into a 10-mer PNA oligomer using standard Fmoc chemistry for solid-phase synthesis. Oligomerization proceeded smoothly and the HPLC and MALDI-TOF MS analyses indicated that there was no remaining MMPM on the sU nucleobase. The new PNA monomers reported here would facilitate a wide range of applications, such as antigene PNAs and DNA nanotechnologies. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2017.06.015