(2S,3aR,6S,7aR)-1-benzyl 2-methyl 3a,6-dihydroxy-3,3a,7,7a-tetrahydro-1H-indole-1,2(2H,6H)-dicarboxylate | 185394-34-7

• 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,6S,7aR)-1-benzyl 2-methyl 3a,6-dihydroxy-3,3a,7,7a-tetrahydro-1H-indole-1,2(2H,6H)-dicarboxylate
• CAS: 185394-34-7
• 化学式: C₁₈H₂₁NO₆
• 分子量: 347.368
• InChiKey: PAPGKMHHWAJWPS-FSZRXZPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.99
• 重原子数：
  25.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  96.3
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (2S,3aR,6S,7aR)-1-benzyl 2-methyl 3a,6-dihydroxy-3,3a,7,7a-tetrahydro-1H-indole-1,2(2H,6H)-dicarboxylate 在 4-二甲氨基吡啶 、 palladium diacetate 、 氧气 、 tetraphenylporphyrin 、 溶剂黄146 、 三乙胺 、 三苯基膦 、 锌 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 13.0h， 生成 (2S-(2β,3aβ,4β,7β,7aβ))-2,3,3a,4,7,7a-hexahydro-3a,4,7-trihydroxy-1H-indole-1,2-dicarboxylic acid 1-benzyl 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：

  (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 sodium tetrahydroborate 、 cerium(III) chloride 作用下， 以 甲醇 为溶剂， 反应 0.17h， 以94%的产率得到(2S,3aR,6S,7aR)-1-benzyl 2-methyl 3a,6-dihydroxy-3,3a,7,7a-tetrahydro-1H-indole-1,2(2H,6H)-dicarboxylate
  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

文献信息

• Synthesis of Hydroxylated Bicyclic Amino Acids from <scp>l</scp>-Tyrosine: Octahydro-1<i>H</i>-indole Carboxylates
  作者：Joshua G. Pierce、Dhanalakshmi Kasi、Makoto Fushimi、Anthony Cuzzupe、Peter Wipf

  DOI：10.1021/jo801552j

  日期：2008.10.3

  A stereoselective approach to polyhydroxylated L-Choi derivatives has been developed. The oxidative cyclization Of L-tyrosine was optimized to avoid partial racemization and to allow a more efficient scale-up.