(N-tert-butoxycarbonyl-1-carbobenzyloxy-2-iodo-L-tryptophanyl)-L-isoleucine methyl ester | 1053208-71-1

• 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: (N-tert-butoxycarbonyl-1-carbobenzyloxy-2-iodo-L-tryptophanyl)-L-isoleucine methyl ester
• 英文别名: benzyl 2-iodo-3-[(2S)-3-[[(2S,3S)-1-methoxy-3-methyl-1-oxopentan-2-yl]amino]-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-oxopropyl]indole-1-carboxylate
• CAS: 1053208-71-1
• 化学式: C₃₁H₃₈IN₃O₇
• 分子量: 691.563
• InChiKey: DSGTXJMBJXXTDE-QXWFJRNPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  42
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  125
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (N-tert-butoxycarbonyl-1-carbobenzyloxy-2-iodo-L-tryptophanyl)-L-isoleucine methyl ester 在 potassium phosphate 、 copper(l) iodide 、 trans-1,2-Diaminocyclohexane 作用下， 以 甲苯 为溶剂， 以67%的产率得到4-O-benzyl 3-O-tert-butyl (2S)-2-[[(2S,3S)-1-methoxy-3-methyl-1-oxopentan-2-yl]carbamoyl]-1,2-dihydropyrrolo[2,3-b]indole-3,4-dicarboxylate
  参考文献：
  名称：

  Copper-Catalyzed Cyclization of Iodo-tryptophans: A Straightforward Synthesis of Pyrroloindoles

  摘要：

  Pyrroloindoles are a key structural motif found in a wide number of biologically active alkaloids. Intramolecular copper-catalyzed coupling of readily accessible 2-iodo-tryptophan derivatives occurs in excellent yield, affording a wide range of polysubstituted, enantioenriched tetrahydropyrrolo[2,3-b]indoles. Diketopiperazines are also suitable substrates for this cyclization reaction, which affords a straightforward entry to tetra- to hepta-polycyclic systems.

  DOI：

  10.1021/ol8015513
• 作为产物：
  描述：

  N-tert-butoxycarbonyl-L-tryptophanyl-L-isoleucine methyl ester 在 mercury(II) trifluoroacetate 、 碘 作用下， 以 二氯甲烷 为溶剂， 以42%的产率得到(N-tert-butoxycarbonyl-1-carbobenzyloxy-2-iodo-L-tryptophanyl)-L-isoleucine methyl ester
  参考文献：
  名称：

  Copper-Catalyzed Cyclization of Iodo-tryptophans: A Straightforward Synthesis of Pyrroloindoles

  摘要：

  Pyrroloindoles are a key structural motif found in a wide number of biologically active alkaloids. Intramolecular copper-catalyzed coupling of readily accessible 2-iodo-tryptophan derivatives occurs in excellent yield, affording a wide range of polysubstituted, enantioenriched tetrahydropyrrolo[2,3-b]indoles. Diketopiperazines are also suitable substrates for this cyclization reaction, which affords a straightforward entry to tetra- to hepta-polycyclic systems.

  DOI：

  10.1021/ol8015513