tribenzyl (2R,3aS,8bS)-2-methyl-3a,8b-dihydro-1H-pyrrolo[2,3-b]indole-2,3,4-tricarboxylate | 200716-92-3

• 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: tribenzyl (2R,3aS,8bS)-2-methyl-3a,8b-dihydro-1H-pyrrolo[2,3-b]indole-2,3,4-tricarboxylate
• CAS: 200716-92-3
• 化学式: C₃₅H₃₂N₂O₆
• 分子量: 576.649
• InChiKey: CCYWWWBSFFXNDO-UJHKNFJSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  43
• 可旋转键数：
  10
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  85.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tribenzyl (2R,3aS,8bS)-2-methyl-3a,8b-dihydro-1H-pyrrolo[2,3-b]indole-2,3,4-tricarboxylate 在 palladium on activated charcoal 氢气 、 三氟乙酸 作用下， 以 乙醇 为溶剂， 反应 4.5h， 生成 alpha-甲基-D-色氨酸
  参考文献：
  名称：

  Tetrahydro-pyrrolo-[2,3-b]indole-1,2,8-tricarboxylic acid ester in enantiospecific preparation of α-methyltryptophan: application in the preparation of carbon-14 labeled PD 145942 and PD 154075

  摘要：

  [2R-(2 alpha, 3a beta, 8a beta)]-2,3,3a,8a-Tetrahydro-pyrrolo[2.3-b]indole-1,2,8-tricarboxylic acid-1,8-dibenzyl ester 2-methyl ester, its [2S-(2 beta, 3a alpha, 8a alpha)]-isomer, and the tribenzyl ester analogs were prepared. From these [2,3-b]indole-1,2,8-tricarboxylic acid esters we accomplished a simple, high yielding preparation of enantiopure alpha-methyltryptophan and methyl ester derivatives. Using this protocol, we inexpensively made (R)-alpha-[C-14]methyltryptophan methyl ester, and in subsequent reactions converted it into [1-(2-hydroxy-cyclohexylcarbamoyl)-2-(1H-indol-3-yl)-1-[C-14]methylethyl]carbamic acid adamantan-2-yl ester (PD 145942) and [2-(1H-indole-3-yl)-1-[C-14]methyl-1(1-phenyl-ethylcarbamoyl)-ethyl]carbamic acid benzofuran-2-yl methyl ester (PD 154075). Both of these compounds are drug candidates in preclinical study for the treatment of anxiety and emesis respectively.

  DOI：

  10.1002/(sici)1099-1344(199712)39:12<1019::aid-jlcr43>3.0.co;2-t
• 作为产物：
  描述：

  N-苄氧羰基-D-色氨酸 在 sodium carbonate 、 caesium carbonate 、 三氟乙酸 、 lithium hexamethyldisilazane 作用下， 以 1,4-二氧六环 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 105.0h， 生成 tribenzyl (2R,3aS,8bS)-2-methyl-3a,8b-dihydro-1H-pyrrolo[2,3-b]indole-2,3,4-tricarboxylate
  参考文献：
  名称：

  Tetrahydro-pyrrolo-[2,3-b]indole-1,2,8-tricarboxylic acid ester in enantiospecific preparation of α-methyltryptophan: application in the preparation of carbon-14 labeled PD 145942 and PD 154075

  摘要：

  [2R-(2 alpha, 3a beta, 8a beta)]-2,3,3a,8a-Tetrahydro-pyrrolo[2.3-b]indole-1,2,8-tricarboxylic acid-1,8-dibenzyl ester 2-methyl ester, its [2S-(2 beta, 3a alpha, 8a alpha)]-isomer, and the tribenzyl ester analogs were prepared. From these [2,3-b]indole-1,2,8-tricarboxylic acid esters we accomplished a simple, high yielding preparation of enantiopure alpha-methyltryptophan and methyl ester derivatives. Using this protocol, we inexpensively made (R)-alpha-[C-14]methyltryptophan methyl ester, and in subsequent reactions converted it into [1-(2-hydroxy-cyclohexylcarbamoyl)-2-(1H-indol-3-yl)-1-[C-14]methylethyl]carbamic acid adamantan-2-yl ester (PD 145942) and [2-(1H-indole-3-yl)-1-[C-14]methyl-1(1-phenyl-ethylcarbamoyl)-ethyl]carbamic acid benzofuran-2-yl methyl ester (PD 154075). Both of these compounds are drug candidates in preclinical study for the treatment of anxiety and emesis respectively.

  DOI：

  10.1002/(sici)1099-1344(199712)39:12<1019::aid-jlcr43>3.0.co;2-t

文献信息

• Tetrahydro-pyrrolo-[2,3-b]indole-1,2,8-tricarboxylic acid ester in enantiospecific preparation of α-methyltryptophan: application in the preparation of carbon-14 labeled PD 145942 and PD 154075
  作者：I. Victor Ekhato、Yun Huang

  DOI：10.1002/(sici)1099-1344(199712)39:12<1019::aid-jlcr43>3.0.co;2-t

  日期：1997.12

  [2R-(2 alpha, 3a beta, 8a beta)]-2,3,3a,8a-Tetrahydro-pyrrolo[2.3-b]indole-1,2,8-tricarboxylic acid-1,8-dibenzyl ester 2-methyl ester, its [2S-(2 beta, 3a alpha, 8a alpha)]-isomer, and the tribenzyl ester analogs were prepared. From these [2,3-b]indole-1,2,8-tricarboxylic acid esters we accomplished a simple, high yielding preparation of enantiopure alpha-methyltryptophan and methyl ester derivatives. Using this protocol, we inexpensively made (R)-alpha-[C-14]methyltryptophan methyl ester, and in subsequent reactions converted it into [1-(2-hydroxy-cyclohexylcarbamoyl)-2-(1H-indol-3-yl)-1-[C-14]methylethyl]carbamic acid adamantan-2-yl ester (PD 145942) and [2-(1H-indole-3-yl)-1-[C-14]methyl-1(1-phenyl-ethylcarbamoyl)-ethyl]carbamic acid benzofuran-2-yl methyl ester (PD 154075). Both of these compounds are drug candidates in preclinical study for the treatment of anxiety and emesis respectively.