(5S,8S,11S,14R,17S,19aS)-11-(4-Amino-butyl)-5,17-dibenzyl-8-((R)-1-hydroxy-ethyl)-14-(1H-indol-3-ylmethyl)-tetradecahydro-3a,6,9,12,15,18-hexaaza-cyclopentacyclooctadecene-4,7,10,13,16,19-hexaone | 77236-35-2

• 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: (5S,8S,11S,14R,17S,19aS)-11-(4-Amino-butyl)-5,17-dibenzyl-8-((R)-1-hydroxy-ethyl)-14-(1H-indol-3-ylmethyl)-tetradecahydro-3a,6,9,12,15,18-hexaaza-cyclopentacyclooctadecene-4,7,10,13,16,19-hexaone
• 英文别名: L-363,301；c[Pro-Phe-D-Trp-Lys-Thr-Phe]；c<-Pro-Phe-D-Trp-Lys-Thr-Phe->；cyclo[Pro-Phe-D-Trp-Lys-Thr-Phe]；cyclo(Pro-Phe-D-Trp-Lys-Thr-Phe)；(3S,6S,9S,12R,15S,18S)-9-(4-aminobutyl)-3,15-dibenzyl-6-[(1R)-1-hydroxyethyl]-12-(1H-indol-3-ylmethyl)-1,4,7,10,13,16-hexazabicyclo[16.3.0]henicosane-2,5,8,11,14,17-hexone
• CAS: 77236-35-2
• 化学式: C₄₄H₅₄N₈O₇
• 分子量: 806.962
• InChiKey: FHSGULRVYLHXFO-FFNFELIASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  59
• 可旋转键数：
  11
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  228
• 氢给体数：
  8
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  cyclo 在 palladium on carbon 、 氢气 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 12.0h， 以70%的产率得到(5S,8S,11S,14R,17S,19aS)-11-(4-Amino-butyl)-5,17-dibenzyl-8-((R)-1-hydroxy-ethyl)-14-(1H-indol-3-ylmethyl)-tetradecahydro-3a,6,9,12,15,18-hexaaza-cyclopentacyclooctadecene-4,7,10,13,16,19-hexaone
  参考文献：
  名称：

  Cyclic Peptide Synthesis with Thioacids

  摘要：

  C-Terminal amino acid 9-fluorenylmethylthioesters may be carried through Boc chemistry solution phase peptide synthesis sequences. After insertion of the final residue in the form of an Fmoc carbamate, treatment with piperidine releases a seco-peptide as a C-terminal thioacid that on treatment with Sangers reagent undergoes cyclization to a cyclic peptide. Cyclic penta- and hexapeptides have been synthesized in this manner, as has a cyclic glycopeptide. Functional group compatibility with alcohols and carboxylic acids is demonstrated.

  DOI：

  10.1021/ol101201w

文献信息

• Cyclic Peptide Synthesis with Thioacids
  作者：Kaname Sasaki、David Crich

  DOI：10.1021/ol101201w

  日期：2010.7.16

  C-Terminal amino acid 9-fluorenylmethylthioesters may be carried through Boc chemistry solution phase peptide synthesis sequences. After insertion of the final residue in the form of an Fmoc carbamate, treatment with piperidine releases a seco-peptide as a C-terminal thioacid that on treatment with Sangers reagent undergoes cyclization to a cyclic peptide. Cyclic penta- and hexapeptides have been synthesized in this manner, as has a cyclic glycopeptide. Functional group compatibility with alcohols and carboxylic acids is demonstrated.