(S)-4-((2S,4R)-4-Allyloxycarbonyl-2-hydroxy-5-phenyl-pentyl)-3-tert-butylcarbamoyl-piperazine-1-carboxylic acid tert-butyl ester | 497166-08-2

• 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: (S)-4-((2S,4R)-4-Allyloxycarbonyl-2-hydroxy-5-phenyl-pentyl)-3-tert-butylcarbamoyl-piperazine-1-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl (3S)-4-[(2S,4R)-4-benzyl-2-hydroxy-5-oxo-5-prop-2-enoxypentyl]-3-(tert-butylcarbamoyl)piperazine-1-carboxylate
• CAS: 497166-08-2
• 化学式: C₂₉H₄₅N₃O₆
• 分子量: 531.693
• InChiKey: IUYAMUWIOXHFKR-SGNDLWITSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  38
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  108
• 氢给体数：
  2
• 氢受体数：
  7

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  ——	(S)-3-tert-Butylcarbamoyl-4-((2S,4R)-4-carboxy-2-hydroxy-5-phenyl-pentyl)-piperazine-1-carboxylic acid tert-butyl ester	1027528-21-7	C26H41N3O6	491.628
  ——	dihydro-5(S)-<<4-<(1,1-dimethylethoxy)carbonyl>-2(S)-(N-tert-butylcarbamoyl)piperazinyl>methyl>-3(R)-(phenylmethyl)-3(2H)-furanone	150323-36-7	C26H39N3O5	473.613

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  茚地那韦	indinavir	150378-17-9	C36H47N5O4	613.8

反应信息

• 作为反应物：
  描述：

  3-吡啶甲醛 、 (1S,2R)-(-)-1-氨基-2-茚醇 、 (S)-4-((2S,4R)-4-Allyloxycarbonyl-2-hydroxy-5-phenyl-pentyl)-3-tert-butylcarbamoyl-piperazine-1-carboxylic acid tert-butyl ester 生成 茚地那韦
  参考文献：
  名称：

  Combinatorial diversification of indinavir: in vivo mixture dosing of an HIV protease inhibitor library

  摘要：

  An efficient combination solution-phase/solid-phase route enabling the diversification of the P-1', P-2', and P-3 subsites of indinavir has been established. The synthetic sequence can facilitate the rapid generation of HIV protease inhibitors possessing more favorable pharmacokinetic properties as well as enhanced potencies. Multiple compound dosing in vivo may also accelerate the identification of potential drug candidates. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00276-6
• 作为产物：
  描述：

  dihydro-5(S)-<<4-<(1,1-dimethylethoxy)carbonyl>-2(S)-(N-tert-butylcarbamoyl)piperazinyl>methyl>-3(R)-(phenylmethyl)-3(2H)-furanone 在 lithium hydroxide 、 碳酸氢钠 作用下， 以 乙二醇二甲醚 、 N,N-二甲基甲酰胺 为溶剂， 生成 (S)-4-((2S,4R)-4-Allyloxycarbonyl-2-hydroxy-5-phenyl-pentyl)-3-tert-butylcarbamoyl-piperazine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Combinatorial diversification of indinavir: in vivo mixture dosing of an HIV protease inhibitor library

  摘要：

  An efficient combination solution-phase/solid-phase route enabling the diversification of the P-1', P-2', and P-3 subsites of indinavir has been established. The synthetic sequence can facilitate the rapid generation of HIV protease inhibitors possessing more favorable pharmacokinetic properties as well as enhanced potencies. Multiple compound dosing in vivo may also accelerate the identification of potential drug candidates. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00276-6

文献信息

• Combinatorial library of indinavir analogues: replacement for the aminoindanol at P2′
  作者：Subharekha Raghavan、Zheng Yang、Ralph T. Mosley、William A. Schleif、Lori Gabryelski、David B. Olsen、Mark Stahlhut、Lawrence C. Kuo、Emilio A. Emini、Kevin T. Chapman、James R. Tata

  DOI：10.1016/s0960-894x(02)00632-7

  日期：2002.10

  A 1X22X41 combinatorial library or 902 compounds of indinavir analogues was synthesized on the solid support to identify a replacement for the aminoindanol moiety at P-2'. 2,6-Dimethyl-4-hydroxy phenol was discovered to be a good replacement for aminoindanol. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Combinatorial diversification of indinavir: in vivo mixture dosing of an HIV protease inhibitor library
  作者：Thomas A Rano、Yuan Cheng、Tracy T Huening、Fengqi Zhang、William A Schleif、Lori Gabryelski、David B Olsen、Lawrence C Kuo、Jiunn H Lin、Xin Xu、Timothy V Olah、Debra A McLoughlin、Richard King、Kevin T Chapman、James R Tata

  DOI：10.1016/s0960-894x(00)00276-6

  日期：2000.7

  An efficient combination solution-phase/solid-phase route enabling the diversification of the P-1', P-2', and P-3 subsites of indinavir has been established. The synthetic sequence can facilitate the rapid generation of HIV protease inhibitors possessing more favorable pharmacokinetic properties as well as enhanced potencies. Multiple compound dosing in vivo may also accelerate the identification of potential drug candidates. (C) 2000 Elsevier Science Ltd. All rights reserved.