(2R,3aR,6R,7aR)-6-Acetoxy-octahydro-indole-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester | 543700-92-1

• 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: (2R,3aR,6R,7aR)-6-Acetoxy-octahydro-indole-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester
• CAS: 543700-92-1
• 化学式: C₁₇H₂₇NO₆
• 分子量: 341.404
• InChiKey: NOLHGECXZJAEMN-AAVRWANBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.27
• 重原子数：
  24.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  82.14
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (2R,3aR,6R,7aR)-6-Acetoxy-octahydro-indole-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester 在 N-甲基吗啉 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 (2R,3aR,6R,7aR)-6-Acetoxy-1-((R)-2-tert-butoxycarbonylamino-4-methyl-pentanoyl)-octahydro-indole-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Syntheses of Both the Putative and Revised Structures of Aeruginosin EI461 Bearing a New Bicyclic α-Amino Acid

  摘要：

  [GRAPHICS]The putative structure of the naturally occurring aquatic peptide aeruginosin EI461 has been prepared from D-tyrosine. A corrected structure for aeruginosin EI461 is proposed, and the structure is proven by synthesis, which was accomplished using the new alpha-amino acid (2S,-3aR,6R,7aR)-6-hydroxy-2-carboxyoctahydroindole, prepared from L-tyrosine. Succesive couplings of the dipeptide D-Leu-3a,7a-diepi-L-Choi with L-Hpla and NH4OH and a deprotection step gave aeruginosin EI461.

  DOI：

  10.1021/ol0273250
• 作为产物：
  描述：

  (2R,3aR,7aR)-6-Oxo-octahydro-indole-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 作用下， 以 甲醇 为溶剂， 生成 (2R,3aR,6R,7aR)-6-Acetoxy-octahydro-indole-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester
  参考文献：
  名称：

  Syntheses of Both the Putative and Revised Structures of Aeruginosin EI461 Bearing a New Bicyclic α-Amino Acid

  摘要：

  [GRAPHICS]The putative structure of the naturally occurring aquatic peptide aeruginosin EI461 has been prepared from D-tyrosine. A corrected structure for aeruginosin EI461 is proposed, and the structure is proven by synthesis, which was accomplished using the new alpha-amino acid (2S,-3aR,6R,7aR)-6-hydroxy-2-carboxyoctahydroindole, prepared from L-tyrosine. Succesive couplings of the dipeptide D-Leu-3a,7a-diepi-L-Choi with L-Hpla and NH4OH and a deprotection step gave aeruginosin EI461.

  DOI：

  10.1021/ol0273250