2'-deoxy-2'-C-α-propyluridine | 158718-45-7

• 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: 2'-deoxy-2'-C-α-propyluridine
• 英文别名: 1-[(2R,3R,4S,5R)-4-hydroxy-5-(hydroxymethyl)-3-propyloxolan-2-yl]pyrimidine-2,4-dione
• CAS: 158718-45-7
• 化学式: C₁₂H₁₈N₂O₅
• 分子量: 270.285
• InChiKey: PFYVUBVFHQARDN-DEKFOEGESA-N

物化性质

• 密度：
  1.332±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  99.1
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2'-deoxy-2'-C-α-propyluridine 在 4-二甲氨基吡啶 、 2,4,6-三异丙基苯磺酰氯 、 silver nitrate 、 triethylamine tris(hydrogen fluoride) 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 68.0h， 生成 N⁴-acetyl-2'-deoxy-2'-C-α-propylcytidine
  参考文献：
  名称：

  Synthesis of 2‘-C-α-(Hydroxyalkyl) and 2‘-C-α-Alkylcytidine Phosphoramidites:  Analogues for Probing Solvent Interactions with RNA

  摘要：

  Nucleoside analogues bearing 2'-C-alpha-(hydroxyalkyl) and 2'-C-alpha-alkyl substitutes have numerous applications in RNA chemistry and biology. In particular, they provide a strategy to probe the interaction between the 2'-hydroxyl group of RNA and water. To incorporate these nucleoside analogues into oligonucleotides for studies of the group II intron (Gordon, P. M.; Fong, R.; Deb, S.; Li, N.-S.; Schwans, J. P.; Ye, J.-D.; Piccirilli, J. A. Chem. Biol. 2004, 11, 237), we synthesized six new phosphoramidite derivatives of 2'-deoxy-2'-C-alpha-(hydroxyalkyl)cytidine (36: R = -(CH2)(2)OH; 38: R = -(CH2)(3)OH; 40: R = -(CH2)(4)OH) and 2'-deoxy-2'-C-alpha-alkylcytidine (37: R = -CH2CH3; 39: R = -(CH2)(2)CH3; 41: R = -(CH2)(3)CH3) from cytidine or uridine via 2'-C-alpha-allylation, followed by alkene and alcohol transformations. Phosphoramidites 36 and 37 were prepared from cytidine in overall yields of 14% (10 steps) and 7% (11 steps), respectively. Phosphoramidites 38 and 39 were prepared from uridine in overall yields of 30% (10 steps) and 13% (11 steps), respectively. Phosphoramidites 40 and 41 were synthesized from uridine in overall yields of 21% (13 steps) and 25% (14 steps), respectively.

  DOI：

  10.1021/jo062002t
• 作为产物：
  描述：

  1-((2R,3R,3aS,9aR)-3-Allyl-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-2-yl)-4-hydroxy-1H-pyrimidin-2-one 在 palladium on activated charcoal 四丁基氟化铵 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 24.17h， 生成 2'-deoxy-2'-C-α-propyluridine
  参考文献：
  名称：

  Synthesis of 2‘-C-α-(Hydroxyalkyl) and 2‘-C-α-Alkylcytidine Phosphoramidites:  Analogues for Probing Solvent Interactions with RNA

  摘要：

  Nucleoside analogues bearing 2'-C-alpha-(hydroxyalkyl) and 2'-C-alpha-alkyl substitutes have numerous applications in RNA chemistry and biology. In particular, they provide a strategy to probe the interaction between the 2'-hydroxyl group of RNA and water. To incorporate these nucleoside analogues into oligonucleotides for studies of the group II intron (Gordon, P. M.; Fong, R.; Deb, S.; Li, N.-S.; Schwans, J. P.; Ye, J.-D.; Piccirilli, J. A. Chem. Biol. 2004, 11, 237), we synthesized six new phosphoramidite derivatives of 2'-deoxy-2'-C-alpha-(hydroxyalkyl)cytidine (36: R = -(CH2)(2)OH; 38: R = -(CH2)(3)OH; 40: R = -(CH2)(4)OH) and 2'-deoxy-2'-C-alpha-alkylcytidine (37: R = -CH2CH3; 39: R = -(CH2)(2)CH3; 41: R = -(CH2)(3)CH3) from cytidine or uridine via 2'-C-alpha-allylation, followed by alkene and alcohol transformations. Phosphoramidites 36 and 37 were prepared from cytidine in overall yields of 14% (10 steps) and 7% (11 steps), respectively. Phosphoramidites 38 and 39 were prepared from uridine in overall yields of 30% (10 steps) and 13% (11 steps), respectively. Phosphoramidites 40 and 41 were synthesized from uridine in overall yields of 21% (13 steps) and 25% (14 steps), respectively.

  DOI：

  10.1021/jo062002t

文献信息

• Antibodies having specificity for nucleic acids
  申请人：——

  公开号：US20030228590A1

  公开（公告）日：2003-12-11

  The present invention relates to antibodies, antibody conjugates, and compositions thereof, methods of antibody synthesis, and applications of antibodies useful for detecting the presence of nucleic acid molecules in vivo, such as in a clinical setting. The antibodies of the invention are also useful as screening agents which allow the selection of candidate therapeutic molecules for optimum bioavailability and/or activity, and as delivery agents for cell and tissue specific delivery of nucleic acid molecules.

  本发明涉及抗体、抗体共轭物及其组合物、抗体合成方法以及抗体在检测体内（如临床环境中）核酸分子存在方面的应用。本发明的抗体还可用作筛选剂，筛选出最佳生物利用度和/或活性的候选治疗分子，还可用作细胞和组织特异性递送核酸分子的递送剂。
• US7071311B2
  申请人：——

  公开号：US7071311B2

  公开（公告）日：2006-07-04
• Synthesis of 2‘-<i>C</i>-α-(Hydroxyalkyl) and 2‘-<i>C</i>-α-Alkylcytidine Phosphoramidites:  Analogues for Probing Solvent Interactions with RNA
  作者：Nan-Sheng Li、Joseph A. Piccirilli

  DOI：10.1021/jo062002t

  日期：2007.2.1

  Nucleoside analogues bearing 2'-C-alpha-(hydroxyalkyl) and 2'-C-alpha-alkyl substitutes have numerous applications in RNA chemistry and biology. In particular, they provide a strategy to probe the interaction between the 2'-hydroxyl group of RNA and water. To incorporate these nucleoside analogues into oligonucleotides for studies of the group II intron (Gordon, P. M.; Fong, R.; Deb, S.; Li, N.-S.; Schwans, J. P.; Ye, J.-D.; Piccirilli, J. A. Chem. Biol. 2004, 11, 237), we synthesized six new phosphoramidite derivatives of 2'-deoxy-2'-C-alpha-(hydroxyalkyl)cytidine (36: R = -(CH2)(2)OH; 38: R = -(CH2)(3)OH; 40: R = -(CH2)(4)OH) and 2'-deoxy-2'-C-alpha-alkylcytidine (37: R = -CH2CH3; 39: R = -(CH2)(2)CH3; 41: R = -(CH2)(3)CH3) from cytidine or uridine via 2'-C-alpha-allylation, followed by alkene and alcohol transformations. Phosphoramidites 36 and 37 were prepared from cytidine in overall yields of 14% (10 steps) and 7% (11 steps), respectively. Phosphoramidites 38 and 39 were prepared from uridine in overall yields of 30% (10 steps) and 13% (11 steps), respectively. Phosphoramidites 40 and 41 were synthesized from uridine in overall yields of 21% (13 steps) and 25% (14 steps), respectively.