(2S,3aR,7aR)-6-oxo-2,3,3a,4,5,6,7,7a-octahydroindole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester | 320748-60-5

• 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: (2S,3aR,7aR)-6-oxo-2,3,3a,4,5,6,7,7a-octahydroindole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester
• CAS: 320748-60-5
• 化学式: C₁₈H₂₁NO₅
• 分子量: 331.368
• InChiKey: JIIGJFOKMNUVAF-BMFZPTHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.31
• 重原子数：
  24.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  72.91
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (2S,3aR,7aR)-6-oxo-2,3,3a,4,5,6,7,7a-octahydroindole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester 在 吡啶 、 L-Selectride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 7.0h， 生成 (2S,3aR,6S,7aR)-6-(tert-Butyl-dimethyl-silanyloxy)-octahydro-indole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester
  参考文献：
  名称：

  Total Synthesis and Stereochemical Revision of (+)-Aeruginosin 298-A

  摘要：

  [GRAPHICS]Novel routes toward both enantiomers of the bicyclic proline surrogate 2-carboxy-6-hydroxyoctahydroindole, i.e., Choi, were developed on the basis of the oxidative cyclization of L-tyrosine. Synthesis of the proposed sequence of (+)-aeruginosin 298-A did not provide the natural product. Incorporation of a D-leucine residue, in contrast, led to the total synthesis of this thrombin inhibitor.

  DOI：

  10.1021/ol006759x
• 作为产物：
  描述：

  (2S,3aR,7aR)-3a-hydroxy-6-oxo-2,3,3a,6,7,7a-hexahydroindole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester 在 platinum(IV) oxide 吡啶 、 4-二甲氨基吡啶 、 氢气 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 溶剂黄146 为溶剂， 反应 24.0h， 生成 (2S,3aR,7aR)-6-oxo-2,3,3a,4,5,6,7,7a-octahydroindole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester
  参考文献：
  名称：

  Total Synthesis and Stereochemical Revision of (+)-Aeruginosin 298-A

  摘要：

  [GRAPHICS]Novel routes toward both enantiomers of the bicyclic proline surrogate 2-carboxy-6-hydroxyoctahydroindole, i.e., Choi, were developed on the basis of the oxidative cyclization of L-tyrosine. Synthesis of the proposed sequence of (+)-aeruginosin 298-A did not provide the natural product. Incorporation of a D-leucine residue, in contrast, led to the total synthesis of this thrombin inhibitor.

  DOI：

  10.1021/ol006759x

文献信息

• Total Synthesis and Structural Revision of Aeruginosin KT608A
  作者：Manuel Scherer、Karl Gademann

  DOI：10.1021/acs.orglett.7b01822

  日期：2017.7.21

  The synthesis of the presumed structure of aeruginosin KT608A was accomplished for the first time. The unusual d-diepi-Choi core was prepared from tyrosine via C–H activation and heterogeneous hydrogenation. Due to differences in the spectral data of synthetic and natural samples, a revised structure featuring l-diepi-Choi was proposed, which was synthesized and confirmed to be identical. On the basis

  铜绿素菌素KT608A的假定结构的合成是第一次完成。酪氨酸通过C–H活化和非均相加氢制得了不寻常的d - dipipi -Choi核。由于在合成的和天然的样品，经修订的结构特征的频谱数据的差异升- diepi -Choi提出，将其合成并确认为相同的。基于这些发现，提出了另外六种铜绿素酶（KT608B，KT650，GH553，DA495A，DA511和KB676）的修订结构。
• Synthesis of a Bis-amino Acid that Creates a Sharp Turn
  作者：Stephen A. Habay、Christian E. Schafmeister

  DOI：10.1021/ol048585f

  日期：2004.9.1

  The synthesis of a new bis-amino acid 1 is presented. This monomer is designed to create a tightly curved structure when assembled into oligomers. The monomer is demonstrated to couple to the previously developed monomer 2 through pairs of amide bonds to create a strongly bent spiro-ladder oligomer. The structure of oligomer 3 was determined in aqueous solution using two-dimensional NMR.