ethyl (5S,8S,11S,14S)-8-benzyl-14-((3aR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-1-(9H-fluoren-9-yl)-11-isobutyl-5-(2-(methylthio)ethyl)-3,6,9,12-tetraoxo-2-oxa-4,7,10,13-tetraazahexadecan-16-oate | 1356547-28-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 英文名称: ethyl (5S,8S,11S,14S)-8-benzyl-14-((3aR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-1-(9H-fluoren-9-yl)-11-isobutyl-5-(2-(methylthio)ethyl)-3,6,9,12-tetraoxo-2-oxa-4,7,10,13-tetraazahexadecan-16-oate
• CAS: 1356547-28-8
• 化学式: C₅₄H₆₆N₄O₁₁S
• 分子量: 979.204
• InChiKey: BGPZQQQVBRPLCC-JKTOGNSZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.81
• 重原子数：
  70.0
• 可旋转键数：
  23.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  188.85
• 氢给体数：
  4.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  ethyl (5S,8S,11S,14S)-8-benzyl-14-((3aR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-1-(9H-fluoren-9-yl)-11-isobutyl-5-(2-(methylthio)ethyl)-3,6,9,12-tetraoxo-2-oxa-4,7,10,13-tetraazahexadecan-16-oate 在 哌啶 、 4-二甲氨基吡啶 、 lithium hydroxide monohydrate 、 水 、 1-羟基苯并三唑 、 N,N'-二异丙基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 生成 (3S,6S,9S,13S)-13-[(3aR,5R,6S,6aR)-2,2-dimethyl-6-phenylmethoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-6-benzyl-3-(2-methylpropyl)-9-(2-methylsulfanylethyl)-1,4,7,10-tetrazacyclotridecane-2,5,8,11-tetrone
  参考文献：
  名称：

  Robust Turn Structures in α₃β Cyclic Tetrapeptides Induced and Controlled by Carbo-β³ Amino Acid

  摘要：

  Designing cyclic tetrapeptides (CTPs), which fold into desired structures, is often a challenging task. While it is difficult to synthesize them, they are also prone to adopt multiple conformations. In this paper we report the synthesis and conformational studies of CTP mimics, having nonconstrained alpha(3)beta motif, that exhibit stable beta- and gamma-turn structures. We also demonstrate the transformation of beta-turn to gamma-turn structure in similar CTPs by inverting the chirality of beta carbon in C-linked-carbo-beta(3)-amino acid (Caa) from R to S.

  DOI：

  10.1021/jo2019834
• 作为产物：
  描述：

  ethyl (5S,8S,11S)-5-benzyl-11-((3aR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-1-(9H-fluoren-9-yl)-8-isobutyl-3,6,9-trioxo-2-oxa-4,7,10-triazatridecan-13-oate 在 哌啶 、 4-二甲氨基吡啶 、 1-羟基苯并三唑 、 N,N'-二异丙基碳二亚胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 生成 ethyl (5S,8S,11S,14S)-8-benzyl-14-((3aR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-1-(9H-fluoren-9-yl)-11-isobutyl-5-(2-(methylthio)ethyl)-3,6,9,12-tetraoxo-2-oxa-4,7,10,13-tetraazahexadecan-16-oate
  参考文献：
  名称：

  Robust Turn Structures in α₃β Cyclic Tetrapeptides Induced and Controlled by Carbo-β³ Amino Acid

  摘要：

  Designing cyclic tetrapeptides (CTPs), which fold into desired structures, is often a challenging task. While it is difficult to synthesize them, they are also prone to adopt multiple conformations. In this paper we report the synthesis and conformational studies of CTP mimics, having nonconstrained alpha(3)beta motif, that exhibit stable beta- and gamma-turn structures. We also demonstrate the transformation of beta-turn to gamma-turn structure in similar CTPs by inverting the chirality of beta carbon in C-linked-carbo-beta(3)-amino acid (Caa) from R to S.

  DOI：

  10.1021/jo2019834