苯并呋喃,4,5,6,7-四氢-2-(1-甲基乙基)- | 258834-89-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 中文名称: 苯并呋喃,4,5,6,7-四氢-2-(1-甲基乙基)-
• 英文名称: N-tert-butoxycarbonyl-6-O-tert-butyldimethylsilyl-2,5-dideoxy-2,5-imino-3,4-O-isopropylidene-D-allitol
• 英文别名: tert-butyl (3aR,4R,6S,6aS)-4-[[tert-butyl(dimethyl)silyl]oxymethyl]-6-(hydroxymethyl)-2,2-dimethyl-3a,4,6,6a-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylate
• CAS: 258834-89-8
• 化学式: C₂₀H₃₉NO₆Si
• 分子量: 417.618
• InChiKey: JMIDDKZIGFHUFO-XUWVNRHRSA-N

物化性质

• 沸点：
  470.6±40.0 °C(Predicted)
• 密度：
  1.037±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.51
• 重原子数：
  28.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  77.46
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  苯并呋喃,4,5,6,7-四氢-2-(1-甲基乙基)- 在 2,6-二叔丁基-4-甲基吡啶 、 potassium carbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 癸二酸聚合氮杂环十三烷-2-酮,六氢-2H-吖庚英-2-酮,1,6-己二胺,己二酸,壬烷二酸和哌嗪
  参考文献：
  名称：

  Transition state analogue inhibitors of protozoan nucleoside hydrolases

  摘要：

  Protozoan parasites are unable to synthesize purines de novo and must rely on purine salvage pathways for their requirements. Nucleoside hydrolases, which are not found in mammals, function as key enzymes in purine salvage in protozoa. Inhibition of these enzymes may disrupt purine supply and specific inhibitors are potential therapeutic agents for the control of protozoan infections. A series of 1,4-dideoxy-1,4-imino-D-ribitols bearing C-bonded aromatic substituents at C-1 have been synthesized, following carbanion additions to the imine 2, and tested as potential nucleoside hydrolase inhibitors. Nucleoside analogues 8, 11, 14, 17, 20, 24-26, 28 exhibit K-i values in the range 0.2-22 mu M against two representative isozymes of protozoan nucleoside hydrolases. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(99)00210-2
• 作为产物：
  描述：

  5-O-tert-butyldimethylsilyl-1,N-dehydro-1,4-dideoxy-1,4-imino-2,3-O-isopropylidene-D-ribitol 在 sodium tetrahydroborate 、 正丁基锂 、 mercuric triflate 、 calcium carbonate 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 54.0h， 生成 苯并呋喃,4,5,6,7-四氢-2-(1-甲基乙基)-
  参考文献：
  名称：

  Transition state analogue inhibitors of protozoan nucleoside hydrolases

  摘要：

  Protozoan parasites are unable to synthesize purines de novo and must rely on purine salvage pathways for their requirements. Nucleoside hydrolases, which are not found in mammals, function as key enzymes in purine salvage in protozoa. Inhibition of these enzymes may disrupt purine supply and specific inhibitors are potential therapeutic agents for the control of protozoan infections. A series of 1,4-dideoxy-1,4-imino-D-ribitols bearing C-bonded aromatic substituents at C-1 have been synthesized, following carbanion additions to the imine 2, and tested as potential nucleoside hydrolase inhibitors. Nucleoside analogues 8, 11, 14, 17, 20, 24-26, 28 exhibit K-i values in the range 0.2-22 mu M against two representative isozymes of protozoan nucleoside hydrolases. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(99)00210-2

文献信息

• Synthesis of <i>bis</i>-Phosphate Iminoaltritol Enantiomers and Structural Characterization with Adenine Phosphoribosyltransferase
  作者：Lawrence D. Harris、Rajesh K. Harijan、Rodrigo G. Ducati、Gary B. Evans、Brett M. Hirsch、Vern L. Schramm

  DOI：10.1021/acschembio.7b00601

  日期：2018.1.19

  Phosphoribosyl transferases (PRTs) are essential in nucleotide synthesis and salvage, amino acid, and vitamin synthesis. Transition state analysis of several PRTs has demonstrated ribocation-like transition states with a partial positive charge residing on the pentose ring. Core chemistry for synthesis of transition state analogues related to the 5-phospho-α-d-ribosyl 1-pyrophosphate (PRPP) reactant

  磷酸核糖基转移酶（PRT）在核苷酸合成和挽救，氨基酸和维生素合成中必不可少。几种PRT的跃迁状态分析表明，核糖化样跃迁状态带有部分正电荷，并存在于戊糖环上。合成这些酶的5-磷酸-α - d-核糖基1-焦磷酸酯（PRPP）反应物相关的过渡态类似物的核心化学方法可以通过将双磷酸酯基立体定向放置在亚氨基糖醇环上来开发。亚胺基和bis提供了阳离子特性-磷酸酯锚定1-和5-磷酸酯结合位点。我们提供了通往这些分子的简便合成途径。将环硝基氧化还原方法应用于与过渡态类似物抑制剂的合成有关的选择性单保护二醇的三种立体异构体的立体控制合成。这些多羟基化的吡咯烷天然产物类似物被双磷酸化以产生5-磷酸核糖基1-磷酸核糖形式的类似物。关键中间体的安全，高产合成代表了通往这些过渡态模拟物的新途径。制备了对映体对的亚氨基二糖醇双磷酸酯（L-DIAB和D-DIAB），并显示出对恶性疟原虫的抑制作用乳清酸磷酸核糖基转移酶和