(2S,3aS,4R,7S,7aR)-7-(tert-Butyl-dimethyl-silanyloxy)-3a,4-dihydroxy-2,3,3a,4,7,7a-hexahydro-indole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester | 185394-41-6

• 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,3aS,4R,7S,7aR)-7-(tert-Butyl-dimethyl-silanyloxy)-3a,4-dihydroxy-2,3,3a,4,7,7a-hexahydro-indole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester
• 英文别名: 1-O-benzyl 2-O-methyl (2S,3aS,4R,7S,7aR)-7-[tert-butyl(dimethyl)silyl]oxy-3a,4-dihydroxy-3,4,7,7a-tetrahydro-2H-indole-1,2-dicarboxylate
• CAS: 185394-41-6
• 化学式: C₂₄H₃₅NO₇Si
• 分子量: 477.63
• InChiKey: IABZFQDDFJQLRY-IYXACIGFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.99
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  106
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2S,3aS,4R,7S,7aR)-7-(tert-Butyl-dimethyl-silanyloxy)-3a,4-dihydroxy-2,3,3a,4,7,7a-hexahydro-indole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester 在 1,3-二甲基-2-苯基-2-磷杂咪唑烷 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 4.0h， 生成 (2S,7S,7aS)-7-(tert-Butyl-dimethyl-silanyloxy)-2,3,7,7a-tetrahydro-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
• 作为产物：
  描述：

  (3aR,6S,6aR,8S,9aS)-6-(tert-Butyl-dimethyl-silanyloxy)-2-ethyl-6,6a,8,9-tetrahydro-3aH-1,3-dioxa-7-aza-2-bora-cyclopenta[d]indene-7,8-dicarboxylic acid 7-benzyl ester 8-methyl ester 在 双氧水 作用下， 以 乙酸乙酯 为溶剂， 反应 1.0h， 生成 (2S,3aS,4R,7S,7aR)-7-(tert-Butyl-dimethyl-silanyloxy)-3a,4-dihydroxy-2,3,3a,4,7,7a-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