benzyl (2S)-3-[3-[(3S)-1-benzyl-3-[2-[(1S)-2-methyl-1-(phenylmethoxycarbonylamino)propyl]-4-(phenylmethoxymethyl)-1,3-oxazol-5-yl]-2-oxoindol-3-yl]-4-methoxyphenyl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate | 1057669-30-3

• 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: benzyl (2S)-3-[3-[(3S)-1-benzyl-3-[2-[(1S)-2-methyl-1-(phenylmethoxycarbonylamino)propyl]-4-(phenylmethoxymethyl)-1,3-oxazol-5-yl]-2-oxoindol-3-yl]-4-methoxyphenyl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate
• CAS: 1057669-30-3
• 化学式: C₆₀H₆₂N₄O₁₀
• 分子量: 999.173
• InChiKey: BGNXTDZBSYVWMC-LZXRYOMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.1
• 重原子数：
  74
• 可旋转键数：
  24
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  168
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  benzyl (2S)-3-[3-[(3S)-1-benzyl-3-[2-[(1S)-2-methyl-1-(phenylmethoxycarbonylamino)propyl]-4-(phenylmethoxymethyl)-1,3-oxazol-5-yl]-2-oxoindol-3-yl]-4-methoxyphenyl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate 在 palladium 10% on activated carbon 、 氢气 、 2,4,6-三甲基吡啶 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以30%的产率得到tert-butyl N-[(2S,7S,10S)-1'-benzyl-15-methoxy-2',9-dioxo-4-(phenylmethoxymethyl)-7-propan-2-ylspiro[17-oxa-5,8-diazatricyclo[10.3.1.13,6]heptadeca-1(15),3,5,12(16),13-pentaene-2,3'-indole]-10-yl]carbamate
  参考文献：
  名称：

  Diazonamide Support Studies: Stereoselective Formation of the C10 Chiral Center in both the CDEFG and AEFG Fragments

  摘要：

  The synthesis of both the AEFG macrolactam and the CDEFG bis-indole/tyrosine units found in the marine natural product diazonamide A is presented. Key to the success of the synthesis is the highly stereoselective direct C-arylation of an oxindole by an aryllead(IV) reagent derived from tyrosine.

  DOI：

  10.1021/ol8014336
• 作为产物：
  描述：

  benzyl (S)-3-(3-((S)-1-benzyl-3-(O-benzyl-N-(((benzyloxy)carbonyl)-L-valyl)-L-seryl)-2-oxoindolin-3-yl)-4-methoxyphenyl)-2-((tert-butoxycarbonyl)amino)propanoate 在 六氯乙烷 、 三乙胺 、 三苯基膦 作用下， 以 乙腈 为溶剂， 反应 5.0h， 以31%的产率得到benzyl (2S)-3-[3-[(3S)-1-benzyl-3-[2-[(1S)-2-methyl-1-(phenylmethoxycarbonylamino)propyl]-4-(phenylmethoxymethyl)-1,3-oxazol-5-yl]-2-oxoindol-3-yl]-4-methoxyphenyl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate
  参考文献：
  名称：

  Diazonamide Support Studies: Stereoselective Formation of the C10 Chiral Center in both the CDEFG and AEFG Fragments

  摘要：

  The synthesis of both the AEFG macrolactam and the CDEFG bis-indole/tyrosine units found in the marine natural product diazonamide A is presented. Key to the success of the synthesis is the highly stereoselective direct C-arylation of an oxindole by an aryllead(IV) reagent derived from tyrosine.

  DOI：

  10.1021/ol8014336

文献信息

• Diazonamide Support Studies: Stereoselective Formation of the C10 Chiral Center in both the CDEFG and AEFG Fragments
  作者：Jinzhen Lin、Brian S. Gerstenberger、Nhu Y T. Stessman、Joseph P. Konopelski

  DOI：10.1021/ol8014336

  日期：2008.9.18

  The synthesis of both the AEFG macrolactam and the CDEFG bis-indole/tyrosine units found in the marine natural product diazonamide A is presented. Key to the success of the synthesis is the highly stereoselective direct C-arylation of an oxindole by an aryllead(IV) reagent derived from tyrosine.