2-cyanoethyl (9-((3aR,4R,6R,6aR)-6-(hydroxymethyl)-2-methoxy-2-methyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-6-(4-nitrophenethoxy)-9H-purin-2-yl)carbamate | 1582752-90-6

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物
• 英文名称: 2-cyanoethyl (9-((3aR,4R,6R,6aR)-6-(hydroxymethyl)-2-methoxy-2-methyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-6-(4-nitrophenethoxy)-9H-purin-2-yl)carbamate
• CAS: 1582752-90-6
• 化学式: C₂₅H₂₇N₇O₁₀
• 分子量: 585.53
• InChiKey: QACOJFARUMCBII-RAZIDGHOSA-N

物化性质

• 密度：
  1.62±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.81
• 重原子数：
  42.0
• 可旋转键数：
  11.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  215.24
• 氢给体数：
  2.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  2-cyanoethyl (9-((3aR,4R,6R,6aR)-6-(hydroxymethyl)-2-methoxy-2-methyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-6-(4-nitrophenethoxy)-9H-purin-2-yl)carbamate 在 水 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.0h， 生成 N²-[(2-cyanoethoxy)carbonyl]-O⁶-[2-(4-nitrophenyl)ethyl]-2′-O-acetylguanosine 、 N²-[(2-cyanoethoxy)carbonyl]-O⁶-[2-(4-nitrophenyl)ethyl]-3′-O-acetylguanosine
  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：

  鸟苷 在 吡啶 、 甲醇 、 4-二甲氨基吡啶 、 ammonium hydroxide 、 三乙胺 、 三苯基膦 、 三氟乙酸 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 24.58h， 生成 2-cyanoethyl (9-((3aR,4R,6R,6aR)-6-(hydroxymethyl)-2-methoxy-2-methyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-6-(4-nitrophenethoxy)-9H-purin-2-yl)carbamate
  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