2,5-bis[(2R,5S)-(2,5-dihydro-3,6-dimethoxy-2-isopropyl-3-pyrazinyl)-methyl]thiophene | 158771-80-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: 2,5-bis[(2R,5S)-(2,5-dihydro-3,6-dimethoxy-2-isopropyl-3-pyrazinyl)-methyl]thiophene
• 英文别名: (2S,5R)-2-[[5-[[(2S,5R)-3,6-dimethoxy-5-propan-2-yl-2,5-dihydropyrazin-2-yl]methyl]thiophen-2-yl]methyl]-3,6-dimethoxy-5-propan-2-yl-2,5-dihydropyrazine
• CAS: 158771-80-3
• 化学式: C₂₄H₃₆N₄O₄S
• 分子量: 476.64
• InChiKey: WDQIDYNBNRXOSH-VNTMZGSJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  33
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  115
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2,5-bis[(2R,5S)-(2,5-dihydro-3,6-dimethoxy-2-isopropyl-3-pyrazinyl)-methyl]thiophene 在 盐酸 、 六甲基二硅氮烷 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 为溶剂， 反应 27.0h， 生成 (S)-3-{5-[(S)-2-Carboxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)-ethyl]-thiophen-2-yl}-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid
  参考文献：
  名称：

  Stereoselective Synthesis of Thiophenedimethyl- and Benzenedimethyl- alpha,alpha'-Bridged Bis(glycines).

  摘要：

  Conformationally constrained cystine analogues have been synthesized which have an all-carbon backbone-chain as a bridge between the alpha,alpha'-positions in two glycine units. An aromatic ring consisting of a 1,2-disubstituted benzene or a 2,3- and 2,5-disubstituted thiophene has been inserted into the bridge. Chiral auxiliaries were used to effect stereoselective syntheses of the (S,S)-bis(amino acids). The latter were further derivatized as Fmoc-derivatives suitable for peptide syntheses. The product 2,3-bis[(2R,5S)-(2,5-dihydro-3,6-dimethoxy- 2-isopropyl-5-pyrazinyl)methyl]-5-methylthiophene has been subjected to X-ray analysis.

  DOI：

  10.3891/acta.chem.scand.51-0392
• 作为产物：
  描述：

  2,5-双(氯甲基)噻吩 、 (R)-2,5-二氢-3,6-二甲氧基-2-异丙基吡嗪 在 正丁基锂 作用下， 生成 2,5-bis[(2R,5S)-(2,5-dihydro-3,6-dimethoxy-2-isopropyl-3-pyrazinyl)-methyl]thiophene 、 2,5-bis[(2R,5S)-(2,5-dihydro-3,6-dimethoxy-2-isopropyl-3-pyrazinyl)-methyl]thiophene
  参考文献：
  名称：

  Stereoselective Synthesis of Thiophenedimethyl- and Benzenedimethyl- alpha,alpha'-Bridged Bis(glycines).

  摘要：

  Conformationally constrained cystine analogues have been synthesized which have an all-carbon backbone-chain as a bridge between the alpha,alpha'-positions in two glycine units. An aromatic ring consisting of a 1,2-disubstituted benzene or a 2,3- and 2,5-disubstituted thiophene has been inserted into the bridge. Chiral auxiliaries were used to effect stereoselective syntheses of the (S,S)-bis(amino acids). The latter were further derivatized as Fmoc-derivatives suitable for peptide syntheses. The product 2,3-bis[(2R,5S)-(2,5-dihydro-3,6-dimethoxy- 2-isopropyl-5-pyrazinyl)methyl]-5-methylthiophene has been subjected to X-ray analysis.

  DOI：

  10.3891/acta.chem.scand.51-0392

文献信息

• Stereoselective Synthesis of Thiophenedimethyl- and Benzenedimethyl- alpha,alpha'-Bridged Bis(glycines).
  作者：Kristin Hammer、Tore Benneche、Håkon Hope、Kjell Undheim、Elemér Fogassy、Charles A. McAuliffe、Stenbjörn Styring、Cecilia Tommos、Kurt Warncke、Bryan R. Wood

  DOI：10.3891/acta.chem.scand.51-0392

  日期：——

  Conformationally constrained cystine analogues have been synthesized which have an all-carbon backbone-chain as a bridge between the alpha,alpha'-positions in two glycine units. An aromatic ring consisting of a 1,2-disubstituted benzene or a 2,3- and 2,5-disubstituted thiophene has been inserted into the bridge. Chiral auxiliaries were used to effect stereoselective syntheses of the (S,S)-bis(amino acids). The latter were further derivatized as Fmoc-derivatives suitable for peptide syntheses. The product 2,3-bis[(2R,5S)-(2,5-dihydro-3,6-dimethoxy- 2-isopropyl-5-pyrazinyl)methyl]-5-methylthiophene has been subjected to X-ray analysis.