N4-[(2-cyanoethyloxy)carbonyl]-3′-O-(tert-butyldimethylsilyl)-5′-O-(4,4′-dimethoxytrityl)cytidine | 1582753-51-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: N4-[(2-cyanoethyloxy)carbonyl]-3′-O-(tert-butyldimethylsilyl)-5′-O-(4,4′-dimethoxytrityl)cytidine
• 英文别名: N⁴-[(2-cyanoethyloxy)carbonyl]-3′-O-(tert-butyldimethylsilyl)-5′-O-(4,4′-dimethoxytrityl)cytidine
• CAS: 1582753-51-2
• 化学式: C₄₀H₄₈N₄O₉Si
• 分子量: 756.928
• InChiKey: VCKAXCZACGRRQU-DCZZOZOESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.38
• 重原子数：
  54.0
• 可旋转键数：
  14.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  163.39
• 氢给体数：
  2.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  N4-[(2-cyanoethyloxy)carbonyl]-3′-O-(tert-butyldimethylsilyl)-5′-O-(4,4′-dimethoxytrityl)cytidine 、 2-氰乙基N,N-二异丙基氯亚磷酰胺 在 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以89%的产率得到N4-[(2-cyanoethyloxy)carbonyl]-3′-O-(tert-butyldimethylsilyl)-5′-O-(4,4′-dimethoxytrityl)cytidine-2′-O-(2-cyanoethyl-N,N-diisopropyl)phosphoramidite
  参考文献：
  名称：

  Solid-Phase Synthesis and Hybrization Behavior of Partially 2′/3′-O-Acetylated RNA Oligonucleotides

  摘要：

  Synthesis of partially 2'/3'-O-acetylated oligoribonucleotides has been accomplished by using a 2'/3'-O-acetyl orthogonal protecting group strategy in which nonnucleophilic strong-base (DBU) labile nucleobase protecting groups and a LTV-light cleavable linker were used. Strong-base stability of the photolabile linker allowed on-column nucleobase and phosphate deprotection, followed by a mild cleavage of the acetylated oligonucleotides from the solid support with UV light. Two 17nt oligonucleotides, which were synthesized possessing one specific internal 2' or 3'-acetyl group, were used as synthetic standards in a recent report from this laboratory detailing the prebiotically plausible ligation of RNA oligonucleotides. In order to further investigate the effect of 2'/3'-O-acetyl groups on the stability of RNA duplex structure, two complementary bis-acetylated RNA oligonucleotides were also expediently obtained with the newly developed protocols. UV melting curves of 2'-O-acetylated RNA duplexes showed a consistent similar to 3.1 degrees C decrease in T-m per 2'-O-acetyl group.

  DOI：

  10.1021/jo5002824
• 作为产物：
  描述：

  4,4'-双甲氧基三苯甲基氯 在 吡啶 、 silver nitrate 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 生成 N4-[(2-cyanoethyloxy)carbonyl]-3′-O-(tert-butyldimethylsilyl)-5′-O-(4,4′-dimethoxytrityl)cytidine
  参考文献：
  名称：

  Solid-Phase Synthesis and Hybrization Behavior of Partially 2′/3′-O-Acetylated RNA Oligonucleotides

  摘要：

  Synthesis of partially 2'/3'-O-acetylated oligoribonucleotides has been accomplished by using a 2'/3'-O-acetyl orthogonal protecting group strategy in which nonnucleophilic strong-base (DBU) labile nucleobase protecting groups and a LTV-light cleavable linker were used. Strong-base stability of the photolabile linker allowed on-column nucleobase and phosphate deprotection, followed by a mild cleavage of the acetylated oligonucleotides from the solid support with UV light. Two 17nt oligonucleotides, which were synthesized possessing one specific internal 2' or 3'-acetyl group, were used as synthetic standards in a recent report from this laboratory detailing the prebiotically plausible ligation of RNA oligonucleotides. In order to further investigate the effect of 2'/3'-O-acetyl groups on the stability of RNA duplex structure, two complementary bis-acetylated RNA oligonucleotides were also expediently obtained with the newly developed protocols. UV melting curves of 2'-O-acetylated RNA duplexes showed a consistent similar to 3.1 degrees C decrease in T-m per 2'-O-acetyl group.

  DOI：

  10.1021/jo5002824