N⁴-acetyl-3',5'-O-(di-tert-butylsilanediyl)-2'-deoxy-2'-C-α-propylcytidine | 929078-07-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N⁴-acetyl-3',5'-O-(di-tert-butylsilanediyl)-2'-deoxy-2'-C-α-propylcytidine
• 英文别名: N-[1-[(4aR,6R,7R,7aS)-2,2-ditert-butyl-7-propyl-4a,6,7,7a-tetrahydro-4H-furo[3,2-d][1,3,2]dioxasilin-6-yl]-2-oxopyrimidin-4-yl]acetamide
• CAS: 929078-07-9
• 化学式: C₂₂H₃₇N₃O₅Si
• 分子量: 451.638
• InChiKey: DTZNFTIQAPOLKO-ZAWLATJESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.97
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  89.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N⁴-acetyl-3',5'-O-(di-tert-butylsilanediyl)-2'-deoxy-2'-C-α-propylcytidine 在 吡啶 、 4-二甲氨基吡啶 、 triethylamine tris(hydrogen fluoride) 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 31.0h， 生成 N-[1-[(2R,3R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-hydroxy-3-propyloxolan-2-yl]-2-oxopyrimidin-4-yl]acetamide
  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：

  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 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 64.0h， 生成 N⁴-acetyl-3',5'-O-(di-tert-butylsilanediyl)-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

文献信息

• 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.