Methyl 2-[2-[(2-methylpropan-2-yl)oxycarbonylamino]ethyl-(2-nitrophenyl)sulfonylamino]acetate | 215056-58-9

• 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 2-[2-[(2-methylpropan-2-yl)oxycarbonylamino]ethyl-(2-nitrophenyl)sulfonylamino]acetate
• CAS: 215056-58-9
• 化学式: C₁₆H₂₃N₃O₈S
• 分子量: 417.44
• InChiKey: RBHQZRVBFQSRKK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  156
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  Methyl 2-[2-[(2-methylpropan-2-yl)oxycarbonylamino]ethyl-(2-nitrophenyl)sulfonylamino]acetate 在 potassium carbonate 、 苯硫酚 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 、 3-羟基-1,2,3-苯并三嗪-4(3H)-酮 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 甘氨酸,N-[(3,4-二氢-5-甲基-2,4-二羰基-1(2H)-嘧啶基)乙酰基]-N-[2-[[(1,1-二甲基乙氧基)羰基]氨基]乙基]-,甲基酯
  参考文献：
  名称：

  Synthesis of achiral and chiral peptide nucleic acid (PNA) monomers using Mitsunobu reaction

  摘要：

  Peptide nucleic acids (PNAs) are intensively studied DNA analogues. We elaborated an efficient procedure for the synthesis of N-, C-protected pseudodipeptides with a reduced peptide bond and then peptide nucleic acid (PNA) monomers, based on the Mitsunobu reaction of N-Boc-beta -amino alcohols with N-o-nitrobenzenesulfonyl-protected (oNBS-protected) amino acid esters. Using the new procedure, we obtained protected PNA monomer backbones with various amino acid side chains. The pseudodipeptide, secondary amine groups were then deprotected by thiolysis, and after appropriate work-up, acylated with thymin-1-ylacetic acid to give the protected monomers. The procedure seems to be of general applicability and allows various modifications of PNA structure by using diverse alcohols and amino acid esters. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00759-1
• 作为产物：
  描述：

  邻硝基苯磺酰氯 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 32.0h， 生成 Methyl 2-[2-[(2-methylpropan-2-yl)oxycarbonylamino]ethyl-(2-nitrophenyl)sulfonylamino]acetate
  参考文献：
  名称：

  PEPTIDE NUCLEIC ACID MONOMER AND A PREPARATION METHOD

  摘要：

  各种实施例中的披荷核酸单体（VI）及利用含有诺磺基起始物制备PNA（VI）的改进工艺相关的披荷核酸单体（VI）及其改进工艺。该工艺包括将氨基酸与诺磺基反应。诺磺保护氨基酸与2-（Boc-氨基）乙基溴烷烷基化以获得中间体。所得中间体的诺磺基被移除以形成PNA骨架。在添加修饰的核碱基后，PNA骨架形成PNA单体（VI）。所得PNA单体表现出手性或无手性几何特性。

  公开号：

  US20180354911A1

文献信息

• PEPTIDE NUCLEIC ACID MONOMER AND A PREPARATION METHOD
  申请人：AMRITA VISHWA VIDYAPEETHAM

  公开号：US20180354911A1

  公开（公告）日：2018-12-13

  The disclosure in various embodiments is related to a peptide nucleic acid monomer (VI) and an improved process for preparation of PNA (VI) using nosyl-group containing starting material. The process includes reacting amino acid with a nosyl group. The nosyl protected amino acid is alkylated with 2-(Boc-amino)ethyl bromide to obtain an intermediate. The nosyl group of the obtained intermediate is removed to form a PNA backbone. The PNA backbone upon addition of a modified nucleobase results in the formation of a PNA monomer (VI). The obtained PNA monomer exhibits either chiral or achiral geometric properties.

  各种实施例中的披荷核酸单体（VI）及利用含有诺磺基起始物制备PNA（VI）的改进工艺相关的披荷核酸单体（VI）及其改进工艺。该工艺包括将氨基酸与诺磺基反应。诺磺保护氨基酸与2-（Boc-氨基）乙基溴烷烷基化以获得中间体。所得中间体的诺磺基被移除以形成PNA骨架。在添加修饰的核碱基后，PNA骨架形成PNA单体（VI）。所得PNA单体表现出手性或无手性几何特性。
• Synthesis of achiral and chiral peptide nucleic acid (PNA) monomers using Mitsunobu reaction
  作者：Bogdan Falkiewicz、Aleksandra S Kołodziejczyk、Bogdan Liberek、Kazimierz Wiśniewski

  DOI：10.1016/s0040-4020(01)00759-1

  日期：2001.9

  Peptide nucleic acids (PNAs) are intensively studied DNA analogues. We elaborated an efficient procedure for the synthesis of N-, C-protected pseudodipeptides with a reduced peptide bond and then peptide nucleic acid (PNA) monomers, based on the Mitsunobu reaction of N-Boc-beta -amino alcohols with N-o-nitrobenzenesulfonyl-protected (oNBS-protected) amino acid esters. Using the new procedure, we obtained protected PNA monomer backbones with various amino acid side chains. The pseudodipeptide, secondary amine groups were then deprotected by thiolysis, and after appropriate work-up, acylated with thymin-1-ylacetic acid to give the protected monomers. The procedure seems to be of general applicability and allows various modifications of PNA structure by using diverse alcohols and amino acid esters. (C) 2001 Elsevier Science Ltd. All rights reserved.