(2S,3aR,6R,7S,7aR)-6-Acetoxy-3a-benzoyloxy-7-(tert-butyl-dimethyl-silanyloxy)-2,3,3a,6,7,7a-hexahydro-indole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester | 185394-47-2

• 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,6R,7S,7aR)-6-Acetoxy-3a-benzoyloxy-7-(tert-butyl-dimethyl-silanyloxy)-2,3,3a,6,7,7a-hexahydro-indole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester
• CAS: 185394-47-2
• 化学式: C₃₃H₄₁NO₉Si
• 分子量: 623.775
• InChiKey: KYEHJUIFQQJNJB-QGSHCBOTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.43
• 重原子数：
  44.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  117.67
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (2S,3aR,6R,7S,7aR)-6-Acetoxy-3a-benzoyloxy-7-(tert-butyl-dimethyl-silanyloxy)-2,3,3a,6,7,7a-hexahydro-indole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester 在 palladium on activated charcoal 1,4-环己二烯 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 (2S,3aR,6R,7S,7aR)-6-Acetoxy-3a-benzoyloxy-7-(tert-butyl-dimethyl-silanyloxy)-2,3,3a,6,7,7a-hexahydro-1H-indole-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Stereodivergent routes from tyrosine to the 7-(R) and 7-(S) diastereomers of the 7-hydroxy-2,3,7,7a-tetrahydroindole ring found in gliotoxin

  摘要：

  Two routes from the oxidative cyclization product 1 derived from tyrosine to methyl 7-(tert-butyldimethylsiloxy)-N-(benzyloxycarbonyl) -2,3,7,7a-tetrahydroindole-2-carboxylate are described. The routes are stereodivergent leading to the 2-S,7-S,7a-S (6) and 2-S,7-R,7a-S-(13) diasteromers. The former stereochemistry corresponds to that present in gliotoxin. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0040-4020(96)00871-x
• 作为产物：
  描述：

  1-O-benzyl 2-O-methyl (2S,3aR,7aR)-3a-benzoyloxy-6-[tert-butyl(dimethyl)silyl]oxy-3,7a-dihydro-2H-indole-1,2-dicarboxylate 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 cerium(III) chloride 、 二甲基二环氧乙烷 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 1,2-二氯乙烷 、 丙酮 为溶剂， 反应 6.58h， 生成 (2S,3aR,6R,7S,7aR)-6-Acetoxy-3a-benzoyloxy-7-(tert-butyl-dimethyl-silanyloxy)-2,3,3a,6,7,7a-hexahydro-indole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester
  参考文献：
  名称：

  Stereodivergent routes from tyrosine to the 7-(R) and 7-(S) diastereomers of the 7-hydroxy-2,3,7,7a-tetrahydroindole ring found in gliotoxin

  摘要：

  Two routes from the oxidative cyclization product 1 derived from tyrosine to methyl 7-(tert-butyldimethylsiloxy)-N-(benzyloxycarbonyl) -2,3,7,7a-tetrahydroindole-2-carboxylate are described. The routes are stereodivergent leading to the 2-S,7-S,7a-S (6) and 2-S,7-R,7a-S-(13) diasteromers. The former stereochemistry corresponds to that present in gliotoxin. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0040-4020(96)00871-x