5'-O-formyl-2',3'-O-isopropylideneadenosine | 97864-71-6

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 5'-O-formyl-2',3'-O-isopropylideneadenosine
• 英文别名: 5'-O-formyl-2',3'-isopropyliden-adenosin；5'-O-Formyl-2',3'-O-isopropyliden-adenosin；O^5'-formyl-O^2'_,O3'-isopropylidene-adenosine；[(3aR,4R,6R,6aR)-4-(6-aminopurin-9-yl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methyl formate
• CAS: 97864-71-6
• 化学式: C₁₄H₁₇N₅O₅
• 分子量: 335.319
• InChiKey: SUFICLOXFQYAIG-QYVSTXNMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.0
• 重原子数：
  24.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  123.61
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为产物：
  描述：

  ((3aR,4R,6R,6aR)-2,2-dimethyl-6-(6-(methylamino)-9H-purin-9-yl)tetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol 在 pyrimido<5,4-g>pteridinetetraone N-oxide 、 乙酸酐 作用下， 以 乙腈 为溶剂， 反应 25.5h， 生成 5'-O-formyl-2',3'-O-isopropylideneadenosine
  参考文献：
  名称：

  N⁶-substituent effect on the photooxidation of 2′,3′-O- isopropylideneadenosines with a pyrimido[5,4-g]pteridinetetraone N-oxide. Chemical evidence for the generation and reactivity of adenosyl cation radicals

  摘要：

  A comparative study on the photooxidation of 2',3'-O-isopropylideneadenosine 1a and its N6-benzoyl, N6-monomethyl, and N6,N6-dimethyl derivatives, 1b-d, with a pyrimido[5,4-g]pteridinetetraone N-oxide (PPO) was carried out. The ease of photooxidative consumption of the adenosines by the PPO is in the order of 1d > 1c > 1a > 1b, which is parallel to their oxidation-peak potentials. Although substrates 1a and 1b underwent oxidative intramolecular cyclisation to the corresponding 5'-O,8-cycloadenosines, 2a and 2b, even in low yield, substrates 1c and 1d were exclusively oxidised at the N6-methyl group to give the corresponding N6-formyl derivatives, 3 and 4, together with minor amounts of demethylated products, 1a and 1c. The present observations provide chemical evidence for the generation and reactivity of adenosyl cation radicals.

  DOI：

  10.1039/p19920001801

文献信息

• N⁶-substituent effect on the photooxidation of 2′,3′-O- isopropylideneadenosines with a pyrimido[5,4-g]pteridinetetraone N-oxide. Chemical evidence for the generation and reactivity of adenosyl cation radicals
  作者：Magoichi Sako、Toru Makino、Yukio Kitade、Kosaku Hirota、Yoshifumi Maki

  DOI：10.1039/p19920001801

  日期：——

  A comparative study on the photooxidation of 2',3'-O-isopropylideneadenosine 1a and its N6-benzoyl, N6-monomethyl, and N6,N6-dimethyl derivatives, 1b-d, with a pyrimido[5,4-g]pteridinetetraone N-oxide (PPO) was carried out. The ease of photooxidative consumption of the adenosines by the PPO is in the order of 1d > 1c > 1a > 1b, which is parallel to their oxidation-peak potentials. Although substrates 1a and 1b underwent oxidative intramolecular cyclisation to the corresponding 5'-O,8-cycloadenosines, 2a and 2b, even in low yield, substrates 1c and 1d were exclusively oxidised at the N6-methyl group to give the corresponding N6-formyl derivatives, 3 and 4, together with minor amounts of demethylated products, 1a and 1c. The present observations provide chemical evidence for the generation and reactivity of adenosyl cation radicals.