(2R)-2-[2-(9H-fluoren-9-ylmethoxycarbonylamino)ethyl-prop-2-enoxycarbonylamino]-6-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoic acid | 1053232-54-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: (2R)-2-[2-(9H-fluoren-9-ylmethoxycarbonylamino)ethyl-prop-2-enoxycarbonylamino]-6-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoic acid
• CAS: 1053232-54-4
• 化学式: C₃₂H₄₁N₃O₈
• 分子量: 595.693
• InChiKey: ZVJYYJRBWCZBCB-HHHXNRCGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  43
• 可旋转键数：
  18
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  144
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (2R)-2-[2-(9H-fluoren-9-ylmethoxycarbonylamino)ethyl-prop-2-enoxycarbonylamino]-6-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoic acid 、 胸腺嘧啶-1-乙酸 生成 H-(T_D-Lys)T-NH2
  参考文献：
  名称：

  A Fmoc-based submonomeric strategy for the solid phase synthesis of optically pure chiral PNAs

  摘要：

  A new submonomeric approach for the Fmoc solid phase synthesis of chiral PNAs is reported here. The design and synthesis of a new D-lysine-based Fmoc submonomer obtained by replacing the nucleobase residue with an Alloc group, compatible with Fmoc chemistry, is described starting from D-lysine and Fmoc-aminoacetaldehyde. The desired submonomer was obtained in high yield with no racemization. The conditions for synthesizing a chiral PNA dimer on solid support by a submonomeric approach have been optimized, allowing to obtain the desired PNA with a very high optical purity. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.05.114
• 作为产物：
  描述：

  N2-(2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)ethyl)-N6-(tert-butoxycarbonyl)-D-lysine 、 氯甲酸烯丙酯 在 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 以91%的产率得到(2R)-2-[2-(9H-fluoren-9-ylmethoxycarbonylamino)ethyl-prop-2-enoxycarbonylamino]-6-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoic acid
  参考文献：
  名称：

  A Fmoc-based submonomeric strategy for the solid phase synthesis of optically pure chiral PNAs

  摘要：

  A new submonomeric approach for the Fmoc solid phase synthesis of chiral PNAs is reported here. The design and synthesis of a new D-lysine-based Fmoc submonomer obtained by replacing the nucleobase residue with an Alloc group, compatible with Fmoc chemistry, is described starting from D-lysine and Fmoc-aminoacetaldehyde. The desired submonomer was obtained in high yield with no racemization. The conditions for synthesizing a chiral PNA dimer on solid support by a submonomeric approach have been optimized, allowing to obtain the desired PNA with a very high optical purity. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.05.114

文献信息

• A Fmoc-based submonomeric strategy for the solid phase synthesis of optically pure chiral PNAs
  作者：Tullia Tedeschi、Stefano Sforza、Francesca Maffei、Roberto Corradini、Rosangela Marchelli

  DOI：10.1016/j.tetlet.2008.05.114

  日期：2008.8

  A new submonomeric approach for the Fmoc solid phase synthesis of chiral PNAs is reported here. The design and synthesis of a new D-lysine-based Fmoc submonomer obtained by replacing the nucleobase residue with an Alloc group, compatible with Fmoc chemistry, is described starting from D-lysine and Fmoc-aminoacetaldehyde. The desired submonomer was obtained in high yield with no racemization. The conditions for synthesizing a chiral PNA dimer on solid support by a submonomeric approach have been optimized, allowing to obtain the desired PNA with a very high optical purity. (C) 2008 Elsevier Ltd. All rights reserved.