3-O-benzyl 4-O-methyl (1S,2R,4S,6S,7R)-6-hydroxy-8,9-dioxa-3-azatricyclo[5.2.2.02,6]undec-10-ene-3,4-dicarboxylate | 185394-37-0

• 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: 3-O-benzyl 4-O-methyl (1S,2R,4S,6S,7R)-6-hydroxy-8,9-dioxa-3-azatricyclo[5.2.2.02,6]undec-10-ene-3,4-dicarboxylate
• CAS: 185394-37-0
• 化学式: C₁₈H₁₉NO₇
• 分子量: 361.351
• InChiKey: QSXRGTVGERDMBF-PQHDGLIZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  94.5
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-O-benzyl 4-O-methyl (1S,2R,4S,6S,7R)-6-hydroxy-8,9-dioxa-3-azatricyclo[5.2.2.02,6]undec-10-ene-3,4-dicarboxylate 在 溶剂黄146 、 锌 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以57%的产率得到(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 4-二甲氨基吡啶 、 palladium diacetate 、 sodium tetrahydroborate 、 cerium(III) chloride 、 氧气 、 tetraphenylporphyrin 、 三乙胺 、 三苯基膦 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 12.17h， 生成 3-O-benzyl 4-O-methyl (1S,2R,4S,6S,7R)-6-hydroxy-8,9-dioxa-3-azatricyclo[5.2.2.02,6]undec-10-ene-3,4-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

• 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
  作者：Todd C Henninger、Michal Sabat、Richard J Sundberg

  DOI：10.1016/0040-4020(96)00871-x

  日期：1996.11

  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