2,6-dichloro-5-(5'-O-[(tert-butyl)dimethylsilyl]-2',3'-O-isopropylidene-α-D-ribofuranosyl)imidazo[1,2-a]pyridine | 177019-73-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并吡啶类
• 英文名称: 2,6-dichloro-5-(5'-O-[(tert-butyl)dimethylsilyl]-2',3'-O-isopropylidene-α-D-ribofuranosyl)imidazo[1,2-a]pyridine
• 英文别名: [(3aS,4R,6R,6aR)-4-(2,6-dichloroimidazo[1,2-a]pyridin-5-yl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methoxy-tert-butyl-dimethylsilane
• CAS: 177019-73-7
• 化学式: C₂₁H₃₀Cl₂N₂O₄Si
• 分子量: 473.472
• InChiKey: PHTWGEJTDVVJAZ-BYNBJNPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.62
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  54.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,6-dichloro-5-(5'-O-[(tert-butyl)dimethylsilyl]-2',3'-O-isopropylidene-α-D-ribofuranosyl)imidazo[1,2-a]pyridine 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 生成 2,6-Dichloro-5-(α-D-ribofuranosyl)imidazo[1,2-a]pyridine
  参考文献：
  名称：

  2，6-二氯咪唑并[1,2-a]吡啶与核糖内酯的缩合反应得到一个新的咪唑并[1,2-a]吡啶C-核苷，其核糖基化位置意外

  摘要：

  通过将锂化的2,6-二氯咪唑并[1,2-a]吡啶（1）与受保护的核糖内酯（2）缩合，然后进行乙酰化反应，可以合成新型核糖基咪唑并[1,2-a]吡啶C-核苷中间核苷4。将该中间体还原性脱乙酰氧基化并脱保护，得到确定为新颖的，出乎意料的2,6-二氯-5-（β-D-核呋喃糖基）咪唑并[1,2-a]吡啶（7）和相应的α-产品（8）。核糖基化的位置是通过远程质子碳去偶联实验确定的。鉴于先前报道的与锂化的咪唑并[1,2-a]吡啶的缩合仅发生在C3位，因此C5的核糖基化完全出乎意料。

  DOI：

  10.1016/0040-4039(96)00292-4
• 作为产物：
  描述：

  5-O-(叔丁基二甲基甲硅烷基)-2,3-O-异亚丙基-D-核酸γ-内酯 在 吡啶 、 三乙基硅烷 、 正丁基锂 、 三氟化硼乙醚 、 胸苷酸 作用下， 反应 16.83h， 生成 2,6-dichloro-5-(5'-O-[(tert-butyl)dimethylsilyl]-2',3'-O-isopropylidene-α-D-ribofuranosyl)imidazo[1,2-a]pyridine
  参考文献：
  名称：

  Synthesis of Imidazo[1,2-a]pyridine C-Nucleosides with an Unexpected Site of Ribosylation

  摘要：

  Several new polychlorinated imidazo[1,2-alpha]pyridine C-nucleosides have been prepared. Lithiated imidazo[1,2-alpha]pyridines were condensed with protected ribonolactones, trapped as 1'-acetoxy derivatives, and these 1'-acetoxy derivatives were reductively deacetoxylated and deprotected to give C-nucleosides. Long-range proton-carbon decoupling experiments were used to determine the actual site of ribosylation and established that the ribose moiety was unexpectedly attached to the C5 position of the imidazo[1,2-alpha]pyridines. This method has provided C-nucleosides, such as 2,6-dichloro-5-(beta-D-ribofuranosyl)imidazo[1,2-alpha]pyridine and 2,6,7-trichloro-5-(beta-D-ribofuranosyl)imidazo[1,2-alpha]pyridine and the corresponding alpha-products.

  DOI：

  10.1021/jo9619342

文献信息

• The condensation of 2,6-dichloroimidazo[1,2-a]pyridine with ribonolactone gives a novel imidazo[1,2-a]pyridine C-nucleoside with an unexpected site of ribosylation
  作者：Kristjan S. Gudmundsson、John C. Drach、Leroy B. Townsend

  DOI：10.1016/0040-4039(96)00292-4

  日期：1996.4

  A novel ribosylated imidazo[1,2-a]pyridine C-nucleoside was synthesized by condensing a lithiated 2,6-dichloroimidazo[1,2-a]pyridine (1) with a protected ribonolactone (2), followed by acetylation to give the intermediate nucleoside 4. This intermediate was reductively deacetoxylated and deprotected to give what was determined to be the novel and unexpected 2,6-dichloro-5-(β-D-ribofuranosyl)imidazo[1

  通过将锂化的2,6-二氯咪唑并[1,2-a]吡啶（1）与受保护的核糖内酯（2）缩合，然后进行乙酰化反应，可以合成新型核糖基咪唑并[1,2-a]吡啶C-核苷中间核苷4。将该中间体还原性脱乙酰氧基化并脱保护，得到确定为新颖的，出乎意料的2,6-二氯-5-（β-D-核呋喃糖基）咪唑并[1,2-a]吡啶（7）和相应的α-产品（8）。核糖基化的位置是通过远程质子碳去偶联实验确定的。鉴于先前报道的与锂化的咪唑并[1,2-a]吡啶的缩合仅发生在C3位，因此C5的核糖基化完全出乎意料。
• Synthesis of Imidazo[1,2-<i>a</i>]pyridine C-Nucleosides with an Unexpected Site of Ribosylation
  作者：Kristjan S. Gudmundsson、John C. Drach、Leroy B. Townsend

  DOI：10.1021/jo9619342

  日期：1997.5.1

  Several new polychlorinated imidazo[1,2-alpha]pyridine C-nucleosides have been prepared. Lithiated imidazo[1,2-alpha]pyridines were condensed with protected ribonolactones, trapped as 1'-acetoxy derivatives, and these 1'-acetoxy derivatives were reductively deacetoxylated and deprotected to give C-nucleosides. Long-range proton-carbon decoupling experiments were used to determine the actual site of ribosylation and established that the ribose moiety was unexpectedly attached to the C5 position of the imidazo[1,2-alpha]pyridines. This method has provided C-nucleosides, such as 2,6-dichloro-5-(beta-D-ribofuranosyl)imidazo[1,2-alpha]pyridine and 2,6,7-trichloro-5-(beta-D-ribofuranosyl)imidazo[1,2-alpha]pyridine and the corresponding alpha-products.