2'-amino-2'-deoxy-2'-N-(fluorenylmethoxycarbonyl)-2'-N-,3'-O-isopropylidene-uridine | 501353-70-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 2'-amino-2'-deoxy-2'-N-(fluorenylmethoxycarbonyl)-2'-N-,3'-O-isopropylidene-uridine
• 英文别名: 9H-fluoren-9-ylmethyl (3aR,4R,6R,6aS)-4-(2,4-dioxopyrimidin-1-yl)-6-(hydroxymethyl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]oxazole-3-carboxylate
• CAS: 501353-70-4
• 化学式: C₂₇H₂₇N₃O₇
• 分子量: 505.527
• InChiKey: OWQYXGXCAVACKR-MSNJVRRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  37
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  118
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  双(二异丙基氨基)(2-氰基乙氧基)膦 、 2'-amino-2'-deoxy-2'-N-(fluorenylmethoxycarbonyl)-2'-N-,3'-O-isopropylidene-uridine 在 二异丙基铵盐四氮唑 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以76%的产率得到2'-amino-2'-deoxy-2'-N-(fluorenylmethoxycarbonyl)-2'-N-,3'-O-isopropylidene-uridin-5'-O-yl cyanoethyl-diisopropylamino-phosphoramidite
  参考文献：
  名称：

  Synthesis of Oligonucleotides with a 2‘-Cap at the 3‘-Terminus via Reversed Phosphoramidites

  摘要：

  [GRAPHICS]A method is presented for the synthesis of single compounds or small combinatorial libraries of oligonucleotides with 2'-acylamido-2'-deoxyuridine residues at the 3'-terminus. Selection experiments identified the residue of anthraquinone-2-carboxylic acid as a "molecular cap" that increases the UV melting point of the duplex (5'-ACGCGU-3')(2) by up to 28degreesC compared to the unmodified control duplex.

  DOI：

  10.1021/ol020212w
• 作为产物：
  描述：

  2’-氨基-D-尿苷 在 camphor-10-sulfonic acid 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 20.0h， 生成 2'-amino-2'-deoxy-2'-N-(fluorenylmethoxycarbonyl)-2'-N-,3'-O-isopropylidene-uridine
  参考文献：
  名称：

  Synthesis of Oligonucleotides with a 2‘-Cap at the 3‘-Terminus via Reversed Phosphoramidites

  摘要：

  [GRAPHICS]A method is presented for the synthesis of single compounds or small combinatorial libraries of oligonucleotides with 2'-acylamido-2'-deoxyuridine residues at the 3'-terminus. Selection experiments identified the residue of anthraquinone-2-carboxylic acid as a "molecular cap" that increases the UV melting point of the duplex (5'-ACGCGU-3')(2) by up to 28degreesC compared to the unmodified control duplex.

  DOI：

  10.1021/ol020212w

文献信息

• Synthesis of Oligonucleotides with a 2‘-Cap at the 3‘-Terminus via Reversed Phosphoramidites
  作者：William H. Connors、Sukunath Narayanan、Olga P. Kryatova、Clemens Richert

  DOI：10.1021/ol020212w

  日期：2003.2.1

  [GRAPHICS]A method is presented for the synthesis of single compounds or small combinatorial libraries of oligonucleotides with 2'-acylamido-2'-deoxyuridine residues at the 3'-terminus. Selection experiments identified the residue of anthraquinone-2-carboxylic acid as a "molecular cap" that increases the UV melting point of the duplex (5'-ACGCGU-3')(2) by up to 28degreesC compared to the unmodified control duplex.