二萘并2,1-d:1,2-f1,3二噻庚英-4-甲醇,2,6-二甲基-α.-苯基-,立体异构体 | 188744-83-4

• 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: 二萘并2,1-d:1,2-f1,3二噻庚英-4-甲醇,2,6-二甲基-α.-苯基-,立体异构体
• 英文名称: (1S)-1-(4-bromophenyl)-5-O-tert-butyldimethylsilyl-1,4-dideoxy-1,4-imino-2,3-O-isopropylidene-D-ribitol
• 英文别名: [(3aS,4S,6R,6aR)-4-(4-bromophenyl)-2,2-dimethyl-4,5,6,6a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyrrol-6-yl]methoxy-tert-butyl-dimethylsilane
• CAS: 188744-83-4
• 化学式: C₂₀H₃₂BrNO₃Si
• 分子量: 442.468
• InChiKey: ZFWNFBPRQPTOMD-XDNAFOTISA-N

物化性质

• 沸点：
  463.8±45.0 °C(Predicted)
• 密度：
  1.157±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.0
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  39.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  二萘并2,1-d:1,2-f1,3二噻庚英-4-甲醇,2,6-二甲基-α.-苯基-,立体异构体 在 palladium diacetate 、 三氟乙酸 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 为溶剂， 反应 6.0h， 生成 4-[(2S,3S,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)pyrrolidin-2-yl]benzonitrile
  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：

  (3AR,4R,6AS)-4-[[[(叔丁酯)二甲基硅烷基]氧基]甲基]四氢-2,2-二甲基-4H-1,3-二氧杂环戊烯并[4,5-C]吡咯 在 2,2,6,6-四甲基哌啶 、 N-氯代丁二酰亚胺 、 正丁基锂 作用下， 以 四氢呋喃 、 正戊烷 为溶剂， 反应 1.5h， 生成 二萘并2,1-d:1,2-f1,3二噻庚英-4-甲醇,2,6-二甲基-α.-苯基-,立体异构体
  参考文献：
  名称：

  N-核糖水解酶和转移酶过渡态抑制剂的合成

  摘要：

  许多带有芳族OH，NH 2，NO 2，CO 2 H和卤素部分的1，4-二脱氧-1，4-亚氨基-1-（S）-（取代的苯基）-d-核糖醇，以及3-吡啶类似物已经合成。关键步骤是芳基锂或芳基格氏试剂与亚胺3的缩合。衍生自受保护的1,4-二脱氧-1,4-亚氨基-d-核糖醇4。

  DOI：

  10.1016/s0040-4020(96)01172-6

文献信息

• Synthesis of transition state inhibitors for N-riboside hydrolases and transferases
  作者：Richard H Furneaux、Gerrit Limberg、Peter C Tyler、Vern L Schramm

  DOI：10.1016/s0040-4020(96)01172-6

  日期：1997.2

  A number of 1,4-dideoxy-1,4-imino-1-(S)-(substituted phenyl)-d-ribitols bearing aromatic OH, NH2, NO2, CO2H and halogeno moieties, and a 3-pyridyl analogue have been synthesized. The key step is the condensation of aryllithium or aryl Grignard reagents with the imine 3; derived from the protected 1,4-dideoxy-1,4-imino-d-ribitol 4.

  许多带有芳族OH，NH 2，NO 2，CO 2 H和卤素部分的1，4-二脱氧-1，4-亚氨基-1-（S）-（取代的苯基）-d-核糖醇，以及3-吡啶类似物已经合成。关键步骤是芳基锂或芳基格氏试剂与亚胺3的缩合。衍生自受保护的1,4-二脱氧-1,4-亚氨基-d-核糖醇4。
• Transition state analogue inhibitors of protozoan nucleoside hydrolases
  作者：Richard H. Furneaux、Vern L. Schramm、Peter C. Tyler

  DOI：10.1016/s0968-0896(99)00210-2

  日期：1999.11

  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.