(2S)-2-[((2R*,5S*,7S*,8aR*)-2-allyl-7-methoxymethoxy-3-oxo-octahydroindolizin-5-ylcarbonyl)amino]pentanedioic acid di(tert-butyl) ester | 1131843-95-2

• 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: (2S)-2-[((2R*,5S*,7S*,8aR*)-2-allyl-7-methoxymethoxy-3-oxo-octahydroindolizin-5-ylcarbonyl)amino]pentanedioic acid di(tert-butyl) ester
• CAS: 1131843-95-2
• 化学式: C₂₇H₄₄N₂O₈
• 分子量: 524.655
• InChiKey: ACFGVHNYYFGFQF-KGMASTOKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.88
• 重原子数：
  37.0
• 可旋转键数：
  11.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  120.47
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (2S)-2-[((2R*,5S*,7S*,8aR*)-2-allyl-7-methoxymethoxy-3-oxo-octahydroindolizin-5-ylcarbonyl)amino]pentanedioic acid di(tert-butyl) ester 在 9-硼双环[3.3.1]壬烷 、 双氧水 、 sodium acetate 作用下， 反应 15.0h， 以65%的产率得到(2S)-2-[((2R*,5S*,7S*,8aR*)-2-(3-hydroxypropyl)-7-methoxymethoxy-3-oxo-octahydroindolizin-5-ylcarbonyl)amino]pentanedioic acid di(tert-butyl) ester
  参考文献：
  名称：

  Synthesis and evaluation of substituted indolizidines as peptidomimetics of RGD tripeptide sequence

  摘要：

  The synthesis of seven peptidomimetics of RGD is presented. The indolizidine building block was obtained by condensation of allylglycine with dimethoxydihydrofuran followed by an intermolecular cyclization. The bicyclic ring was functionalised with a carboxylic acid and a guanidinium appendage. The seven peptidomimetics were evaluated by cell-adhesion assays. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.12.015
• 作为产物：
  描述：

  (2RS,5SR,7SR,8aRS)-2-allyl-7-methoxymethoxy-3-oxo-octahydroindolizine-5-carboxylic acid 、 L-谷氨酸二-叔-丁基酯二苯磺酰亚胺盐 在 N-甲基吗啉 、 氯甲酸异丁酯 作用下， 以 二氯甲烷 为溶剂， 反应 21.0h， 以90%的产率得到(2S)-2-[((2R*,5S*,7S*,8aR*)-2-allyl-7-methoxymethoxy-3-oxo-octahydroindolizin-5-ylcarbonyl)amino]pentanedioic acid di(tert-butyl) ester
  参考文献：
  名称：

  Synthesis and evaluation of substituted indolizidines as peptidomimetics of RGD tripeptide sequence

  摘要：

  The synthesis of seven peptidomimetics of RGD is presented. The indolizidine building block was obtained by condensation of allylglycine with dimethoxydihydrofuran followed by an intermolecular cyclization. The bicyclic ring was functionalised with a carboxylic acid and a guanidinium appendage. The seven peptidomimetics were evaluated by cell-adhesion assays. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.12.015