S-(9-fluorenylmethyl) N-fluorenylmethyloxycarbonyl-δ-O-tert-butyl-D-glutamyl-L-alanyl-D-valyl-L-leucyl-D-thiotryptophanate | 1234549-03-1

• 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: S-(9-fluorenylmethyl) N-fluorenylmethyloxycarbonyl-δ-O-tert-butyl-D-glutamyl-L-alanyl-D-valyl-L-leucyl-D-thiotryptophanate
• 英文别名: tert-butyl (4R)-4-(9H-fluoren-9-ylmethoxycarbonylamino)-5-[[(2S)-1-[[(2R)-1-[[(2S)-1-[[(2R)-1-(9H-fluoren-9-ylmethylsulfanyl)-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-1-oxopropan-2-yl]amino]-5-oxopentanoate
• CAS: 1234549-03-1
• 化学式: C₆₃H₇₂N₆O₉S
• 分子量: 1089.37
• InChiKey: HXTJWPUSTUPSNY-ASUUPISFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.8
• 重原子数：
  79
• 可旋转键数：
  26
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  239
• 氢给体数：
  6
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  S-(9-fluorenylmethyl) N-fluorenylmethyloxycarbonyl-δ-O-tert-butyl-D-glutamyl-L-alanyl-D-valyl-L-leucyl-D-thiotryptophanate 在 三乙基硅烷 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成
  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
• 作为产物：
  描述：

  、 N-芴甲氧羰基-D-谷氨酸 gamma-叔丁酯 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.25h， 以120 mg的产率得到S-(9-fluorenylmethyl) N-fluorenylmethyloxycarbonyl-δ-O-tert-butyl-D-glutamyl-L-alanyl-D-valyl-L-leucyl-D-thiotryptophanate
  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.