(4aS,5S,6aR,7R,8S,10aS,10bR)-methyl 5,8-bis((tert-butyldimethylsilyl)oxy)-7-(((tert-butyldimethylsilyl)oxy)methyl)-3,4a,7,10a-tetramethyl-1-oxo-4a,5,6,6a,7,8,9,10,10a,10b-decahydro-1H-benzo[f]chromene-2-carboxylate | 1338724-12-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (4aS,5S,6aR,7R,8S,10aS,10bR)-methyl 5,8-bis((tert-butyldimethylsilyl)oxy)-7-(((tert-butyldimethylsilyl)oxy)methyl)-3,4a,7,10a-tetramethyl-1-oxo-4a,5,6,6a,7,8,9,10,10a,10b-decahydro-1H-benzo[f]chromene-2-carboxylate
• 英文别名: methyl (4aS,5S,6aR,7R,8S,10aS,10bR)-5,8-bis[[tert-butyl(dimethyl)silyl]oxy]-7-[[tert-butyl(dimethyl)silyl]oxymethyl]-3,4a,7,10a-tetramethyl-1-oxo-6,6a,8,9,10,10b-hexahydro-5H-benzo[f]chromene-2-carboxylate
• CAS: 1338724-12-1
• 化学式: C₃₈H₇₂O₇Si₃
• 分子量: 725.242
• InChiKey: XDAYWSQXOBBKJQ-KMXHEOCMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.04
• 重原子数：
  48
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  80.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (4aS,5S,6aR,7R,8S,10aS,10bR)-methyl 5,8-bis((tert-butyldimethylsilyl)oxy)-7-(((tert-butyldimethylsilyl)oxy)methyl)-3,4a,7,10a-tetramethyl-1-oxo-4a,5,6,6a,7,8,9,10,10a,10b-decahydro-1H-benzo[f]chromene-2-carboxylate 在 甲醇 、 乙酰氯 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 7.5h， 生成 [(1R,2S,5S,6R,7R,9S,10S)-5,9-diacetyloxy-2,6,10-trimethyl-16,18-dioxo-14-pyridin-3-yl-11,15-dioxatetracyclo[8.8.0.02,7.012,17]octadeca-12(17),13-dien-6-yl]methyl acetate
  参考文献：
  名称：

  Total synthesis of pyripyropene A

  摘要：

  The total synthesis of pyripyropene A, a potent ACAT2 inhibitor with high isozyme selectivity, was completed. Key features of the synthetic strategy include Ti(III)-mediated radical cyclization and Peterson olefination for the construction of the AB ring segment and stereoselective dihydro-gamma-pyrone formation (C-ring). The total synthesis provided pyripyropene A in 5.3% overall yield over 17 steps. (C) 2011 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2011.06.084
• 作为产物：
  描述：

  (3S,4aR,5R,6S,8aS)-6-[tert-butyl(dimethyl)silyl]oxy-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-3-hydroxy-2,5,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalene-1-carbaldehyde 在 咪唑 、 4-二甲氨基吡啶 、 异丙基氯化镁 、 戴斯-马丁氧化剂 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 14.75h， 生成 (4aS,5S,6aR,7R,8S,10aS,10bR)-methyl 5,8-bis((tert-butyldimethylsilyl)oxy)-7-(((tert-butyldimethylsilyl)oxy)methyl)-3,4a,7,10a-tetramethyl-1-oxo-4a,5,6,6a,7,8,9,10,10a,10b-decahydro-1H-benzo[f]chromene-2-carboxylate
  参考文献：
  名称：

  Total synthesis of pyripyropene A

  摘要：

  The total synthesis of pyripyropene A, a potent ACAT2 inhibitor with high isozyme selectivity, was completed. Key features of the synthetic strategy include Ti(III)-mediated radical cyclization and Peterson olefination for the construction of the AB ring segment and stereoselective dihydro-gamma-pyrone formation (C-ring). The total synthesis provided pyripyropene A in 5.3% overall yield over 17 steps. (C) 2011 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2011.06.084