p-tolyl-1-thio-5-O-triisopropylsilyl-2-deoxy-α-D-ribofuranoside | 1402737-54-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-tolyl-1-thio-5-O-triisopropylsilyl-2-deoxy-α-D-ribofuranoside
• 英文别名: (2R,3S,5R)-5-(4-methylphenyl)sulfanyl-2-[tri(propan-2-yl)silyloxymethyl]oxolan-3-ol
• CAS: 1402737-54-5
• 化学式: C₂₁H₃₆O₃SSi
• 分子量: 396.667
• InChiKey: IXNFAFFZYKJHDQ-PWRODBHTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.76
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  64
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  p-tolyl-1-thio-5-O-triisopropylsilyl-2-deoxy-α-D-ribofuranoside 、 N-乙酰甘氨酸 在 4-二甲氨基吡啶 、 N,N'-二异丙基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以91%的产率得到p-tolyl-3-O-(N-acetyl)-glycyl-1-thio-5-O-triisopropylsilyl-2-deoxy-α-D-ribofuranoside
  参考文献：
  名称：

  Stereoselective N-Glycosylation of 2-Deoxythioribosides for Fluorescent Nucleoside Synthesis

  摘要：

  An efficient method for the N-2-deoxyribosylation of modified nucleobases by 2-deoxythioriboside donors is reported. In the presence of an in situ silylated nudeobase, thioglycosides can be activated with NIS/HOTf to give nucleosides in high yields and with good beta-selectivity. By tuning the protecting groups on the C3 and CS hydroxyls, alpha/beta ratios ranging from 1.0:4.0 to 4.5:1.0 can be obtained. This strategy is applicable to the synthesis of various nucleosides, including ring-expanded pyrimidine derivatives containing sulfur that have previously been reported in low yields. The utility of this approach is further demonstrated by the synthesis of fluorescent nucleosides analogues such as quinazoline and oxophenothiazine that should find broad utility in DNA-folding and recognition studies.

  DOI：

  10.1021/jo3014929
• 作为产物：
  描述：

  三异丙基氯硅烷 、 p-tolyl-1-thio-2-deoxy-D-ribofuranoside 在 咪唑 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 生成 p-tolyl-1-thio-5-O-triisopropylsilyl-2-deoxy-β-D-ribofuranoside 、 p-tolyl-1-thio-5-O-triisopropylsilyl-2-deoxy-α-D-ribofuranoside
  参考文献：
  名称：

  Synthesis and Solvatochromic Fluorescence of Biaryl Pyrimidine Nucleosides

  摘要：

  Fluorescent pyrimidine analogs containing a fused biphenyl unit were prepared in high yields using stereoselective N-glycosylation and Suzuki-Miyaura cross-coupling reactions. The resulting "push-pull" fluorophores exhibit highly solvatochromic emissions from twisted intramolecular charge-transfer (TICT) states.

  DOI：

  10.1021/ol400930s

文献信息

• Stereoselective <i>N</i>-Glycosylation of 2-Deoxythioribosides for Fluorescent Nucleoside Synthesis
  作者：Guillaume Mata、Nathan W. Luedtke

  DOI：10.1021/jo3014929

  日期：2012.10.19

  An efficient method for the N-2-deoxyribosylation of modified nucleobases by 2-deoxythioriboside donors is reported. In the presence of an in situ silylated nudeobase, thioglycosides can be activated with NIS/HOTf to give nucleosides in high yields and with good beta-selectivity. By tuning the protecting groups on the C3 and CS hydroxyls, alpha/beta ratios ranging from 1.0:4.0 to 4.5:1.0 can be obtained. This strategy is applicable to the synthesis of various nucleosides, including ring-expanded pyrimidine derivatives containing sulfur that have previously been reported in low yields. The utility of this approach is further demonstrated by the synthesis of fluorescent nucleosides analogues such as quinazoline and oxophenothiazine that should find broad utility in DNA-folding and recognition studies.
• Synthesis and Solvatochromic Fluorescence of Biaryl Pyrimidine Nucleosides
  作者：Guillaume Mata、Nathan W. Luedtke

  DOI：10.1021/ol400930s

  日期：2013.5.17

  Fluorescent pyrimidine analogs containing a fused biphenyl unit were prepared in high yields using stereoselective N-glycosylation and Suzuki-Miyaura cross-coupling reactions. The resulting "push-pull" fluorophores exhibit highly solvatochromic emissions from twisted intramolecular charge-transfer (TICT) states.