N⁴-acetyl-3',5'-O-(di-tert-butylsilanediyl)-2'-O-(phenoxythiocarbonyl)cytidine | 929077-97-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N⁴-acetyl-3',5'-O-(di-tert-butylsilanediyl)-2'-O-(phenoxythiocarbonyl)cytidine
• 英文别名: N-[1-[(4aR,6R,7R,7aR)-2,2-ditert-butyl-7-phenoxycarbothioyloxy-4a,6,7,7a-tetrahydro-4H-furo[3,2-d][1,3,2]dioxasilin-6-yl]-2-oxopyrimidin-4-yl]acetamide
• CAS: 929077-97-4
• 化学式: C₂₆H₃₅N₃O₇SSi
• 分子量: 561.731
• InChiKey: UJBDWIKHGWQQHH-ZHHKINOHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.31
• 重原子数：
  38
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  140
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N⁴-acetyl-3',5'-O-(di-tert-butylsilanediyl)-2'-O-(phenoxythiocarbonyl)cytidine 在 sodium tetrahydroborate 、 sodium periodate 、 四氧化锇 、 偶氮二异丁腈 作用下， 以 甲醇 、 水 、 丙酮 、 苯 为溶剂， 反应 4.5h， 生成 N⁴-acetyl-3',5'-O-(di-tert-butylsilanediyl)-2'-deoxy-2'-C-α-(2-hydroxyethyl)cytidine
  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：

  胞苷 在 4-二甲氨基吡啶 、 silver nitrate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.5h， 生成 N⁴-acetyl-3',5'-O-(di-tert-butylsilanediyl)-2'-O-(phenoxythiocarbonyl)cytidine
  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.