1-({2-O-[1-(5-(azidomethyl)-2-nitrophenyl)ethoxy]methyl}-β-D-ribofuranosyl)uracil | 1241387-92-7

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 1-({2-O-[1-(5-(azidomethyl)-2-nitrophenyl)ethoxy]methyl}-β-D-ribofuranosyl)uracil
• 英文别名: 1-[(2R,3R,4R,5R)-3-[1-[5-(azidomethyl)-2-nitrophenyl]ethoxymethoxy]-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
• CAS: 1241387-92-7
• 化学式: C₁₉H₂₂N₆O₉
• 分子量: 478.418
• InChiKey: ZXDKMWHCIFVJME-AVJASUMQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  34
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  178
• 氢给体数：
  3
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  1-({2-O-[1-(5-(azidomethyl)-2-nitrophenyl)ethoxy]methyl}-β-D-ribofuranosyl)uracil 、 4,4'-双甲氧基三苯甲基氯 在 吡啶 作用下， 反应 6.0h， 以93%的产率得到1-(2-O-{[1-(5-(azidomethyl)-2-nitrophenyl)ethoxy]methyl}-5-O-(4,4'-dimethoxytrityl)-β-D-ribofuranosyl)uracil
  参考文献：
  名称：

  Convenient RNA Synthesis Using a Phosphoramidite Possessing a Biotinylated Photocleavable Group

  摘要：

  A convenient RNA synthesis using a biotin streptavidin interaction and a photocleavable protecting group is described. The biotinylated photocleavable group was introduced at the 2'-position of the uridine derivative. Using the phosphoramidite 12, we attempted the synthesis of a 21mer RNA, which is pure enough to show potent RNAi activity compared with a conventionally prepared and HPLC-purified 21mer RNA with the same sequence.

  DOI：

  10.1021/ol101489v
• 作为产物：
  描述：

  在 氟化铵 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以580 mg的产率得到1-({2-O-[1-(5-(azidomethyl)-2-nitrophenyl)ethoxy]methyl}-β-D-ribofuranosyl)uracil
  参考文献：
  名称：

  Convenient RNA Synthesis Using a Phosphoramidite Possessing a Biotinylated Photocleavable Group

  摘要：

  A convenient RNA synthesis using a biotin streptavidin interaction and a photocleavable protecting group is described. The biotinylated photocleavable group was introduced at the 2'-position of the uridine derivative. Using the phosphoramidite 12, we attempted the synthesis of a 21mer RNA, which is pure enough to show potent RNAi activity compared with a conventionally prepared and HPLC-purified 21mer RNA with the same sequence.

  DOI：

  10.1021/ol101489v

文献信息

• Convenient RNA Synthesis Using a Phosphoramidite Possessing a Biotinylated Photocleavable Group
  作者：Kota Tomaya、Mayumi Takahashi、Noriaki Minakawa、Akira Matsuda

  DOI：10.1021/ol101489v

  日期：2010.9.3

  A convenient RNA synthesis using a biotin streptavidin interaction and a photocleavable protecting group is described. The biotinylated photocleavable group was introduced at the 2'-position of the uridine derivative. Using the phosphoramidite 12, we attempted the synthesis of a 21mer RNA, which is pure enough to show potent RNAi activity compared with a conventionally prepared and HPLC-purified 21mer RNA with the same sequence.