{(6S,8R)-8-Azido-8-methyl-4-oxo-6-[(R)-1-((1S,2S,6R,8S)-2,9,9-trimethyl-3,5-dioxa-4-bora-tricyclo[6.1.1.02,6]dec-4-yl)-propylcarbamoyl]-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrimidin-3-yl}-(3-trifluoromethyl-benzyl)-carbamic acid benzyl ester | 437761-09-6

• 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: {(6S,8R)-8-Azido-8-methyl-4-oxo-6-[(R)-1-((1S,2S,6R,8S)-2,9,9-trimethyl-3,5-dioxa-4-bora-tricyclo[6.1.1.02,6]dec-4-yl)-propylcarbamoyl]-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrimidin-3-yl}-(3-trifluoromethyl-benzyl)-carbamic acid benzyl ester
• 英文别名: {(6S,8R)-8-Azido-8-methyl-4-oxo-6-[(R)-1-((1S,2S,6R,8S)-2,9,9-trimethyl-3,5-dioxa-4-bora-tricyclo[6.1.1.0^2,6]dec-4-yl)-propylcarbamoyl]-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrimidin-3-yl}-(3-trifluoromethyl-benzyl)-carbamic acid benzyl ester
• CAS: 437761-09-6
• 化学式: C₃₈H₄₃BF₃N₇O₆
• 分子量: 761.609
• InChiKey: WWJXEKZOAIEMQG-RVCFXXRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.24
• 重原子数：
  55.0
• 可旋转键数：
  10.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  160.75
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  {(6S,8R)-8-Azido-8-methyl-4-oxo-6-[(R)-1-((1S,2S,6R,8S)-2,9,9-trimethyl-3,5-dioxa-4-bora-tricyclo[6.1.1.02,6]dec-4-yl)-propylcarbamoyl]-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrimidin-3-yl}-(3-trifluoromethyl-benzyl)-carbamic acid benzyl ester 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 (6S,8R)-8-methyl-8-[(2-nitrophenyl)carbamoylamino]-4-oxo-3-[[3-(trifluoromethyl)phenyl]methylamino]-N-[(1R)-1-[(1S,2S,6R,8S)-2,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.02,6]decan-4-yl]propyl]-6,7-dihydropyrrolo[1,2-a]pyrimidine-6-carboxamide
  参考文献：
  名称：

  Design and synthesis of bicyclic pyrimidinone-based HCV NS3 protease inhibitors

  摘要：

  A series of bicyclic pyrimidinone-based HCV NS3 protease inhibitors was synthesized via selective C8 position functionalization. Substituted phenylamides and phenylureas were preferred in the S2 binding pocket. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00022-2
• 作为产物：
  描述：

  benzyl (6S,8RS)-6-(anilinocarbonyl)-8-methyl-4-oxo-4,6,7,8-tetrahydropyrrolo[1,2-a]pyrimidin-3-yl[3-(trifluoromethyl)benzyl]carbamate 在 4-二甲氨基吡啶 、 lithium hydroxide 、 N-羟基-7-氮杂苯并三氮唑 、 2,4,6-三异丙基苯磺酰叠氮化物 、 双氧水 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 lithium hexamethyldisilazane 作用下， 以 乙腈 为溶剂， 生成 {(6S,8R)-8-Azido-8-methyl-4-oxo-6-[(R)-1-((1S,2S,6R,8S)-2,9,9-trimethyl-3,5-dioxa-4-bora-tricyclo[6.1.1.02,6]dec-4-yl)-propylcarbamoyl]-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrimidin-3-yl}-(3-trifluoromethyl-benzyl)-carbamic acid benzyl ester
  参考文献：
  名称：

  Design and synthesis of bicyclic pyrimidinone-based HCV NS3 protease inhibitors

  摘要：

  A series of bicyclic pyrimidinone-based HCV NS3 protease inhibitors was synthesized via selective C8 position functionalization. Substituted phenylamides and phenylureas were preferred in the S2 binding pocket. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00022-2