N⁴-[(2-cyanoethoxy)carbonyl]cytidine | 328238-48-8

• 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: N⁴-[(2-cyanoethoxy)carbonyl]cytidine
• 英文别名: 2-cyanoethyl N-[1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-oxopyrimidin-4-yl]carbamate
• CAS: 328238-48-8
• 化学式: C₁₃H₁₆N₄O₇
• 分子量: 340.293
• InChiKey: YLMWSLXAICTFRQ-QCNRFFRDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  165
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N⁴-[(2-cyanoethoxy)carbonyl]cytidine 在 吡啶 、 silver nitrate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 13.0h， 生成 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：

  胞苷 在 甲醇 、 ammonium sulfate 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 51.0h， 生成 N⁴-[(2-cyanoethoxy)carbonyl]cytidine
  参考文献：
  名称：

  核苷酸，第 LXVII 部分，用于核苷和核苷酸化学中碱基保护的 2-氰乙基和 (2-氰基乙氧基)羰基

  摘要：

  在用 2-氰基乙基碳氯酸酯 (5) 或 1-[(2-氰基乙氧基)羰基]-3-甲基-处理时，常见的 2'-脱氧核糖和核糖核苷的氨基官能团被 (2-氰基乙氧基)羰基封闭。 1H-咪唑氯化物 (6) 产生 7, 18, 8, 19, 9 和 20。在 2'-脱氧鸟苷中，酰胺基团在 O6 位被 2-氰乙基 (27) 和 2-( 4-硝基苯基)乙基(31, 32)。关于通过 β-消除裂解 ce/ceoc 和 npe/npeoc 基团的比较动力学研究揭示了有关核碱基不同位点的各种封闭基团的容易性和顺序脱保护的有价值的信息。

  DOI：

  10.1002/1522-2675(20001220)83:12<3198::aid-hlca3198>3.0.co;2-q

文献信息

• Nucleotides, Part LXVII, The 2-Cyanoethyl and (2-Cyanoethoxy)carbonyl Group for Base Protection in Nucleoside and Nucleotide Chemistry
  作者：Claudia Merk、Tilman Reiner、Evgeny Kvasyuk、Wolfgang Pfleiderer

  DOI：10.1002/1522-2675(20001220)83:12<3198::aid-hlca3198>3.0.co;2-q

  日期：2000.12.20

  The amino functions of the common 2′-deoxyribo- and ribonucleosides were blocked by the (2-cyanoethoxy)carbonyl group on treatment with 2-cyanoethyl carbonochloridate (5) or 1-[(2-cyanoethoxy)carbonyl]-3-methyl-1H-imidazolium chloride (6) leading to 7, 18, 8, 19, 9, and 20. In 2′-deoxyguanosine, the amide group was additionally blocked at the O6 position by the 2-cyanoethyl (27) and 2-(4-nitrophenyl)ethyl

  在用 2-氰基乙基碳氯酸酯 (5) 或 1-[(2-氰基乙氧基)羰基]-3-甲基-处理时，常见的 2'-脱氧核糖和核糖核苷的氨基官能团被 (2-氰基乙氧基)羰基封闭。 1H-咪唑氯化物 (6) 产生 7, 18, 8, 19, 9 和 20。在 2'-脱氧鸟苷中，酰胺基团在 O6 位被 2-氰乙基 (27) 和 2-( 4-硝基苯基)乙基(31, 32)。关于通过 β-消除裂解 ce/ceoc 和 npe/npeoc 基团的比较动力学研究揭示了有关核碱基不同位点的各种封闭基团的容易性和顺序脱保护的有价值的信息。
• Solid-Phase Synthesis and Hybrization Behavior of Partially 2′/3′-<i>O</i>-Acetylated RNA Oligonucleotides
  作者：Jianfeng Xu、Colm D. Duffy、Christopher K. W. Chan、John D. Sutherland

  DOI：10.1021/jo5002824

  日期：2014.4.18

  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.