2'-O,3'-O-isopropylidene-5'-O,8-cycloadenosine | 19210-11-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 2'-O,3'-O-isopropylidene-5'-O,8-cycloadenosine
• 英文别名: 5'-O,8-cyclo-2',3'-O-isopropylideneadenosine；2',3'-O-isopropylidene-5'-O-cycloadenosine；O^{2'_,O3'_{-isopropylidene-8,O}5'}-cyclo-adenosine；(4R)-2,2-dimethyl-(3at,13at)-4,5,13,13a-tetrahydro-3aH-4r,13c-epioxido-[1,3]dioxolo[4',5':5,6][1,3]oxazocino[3,2-e]purin-8-ylamine；8,5'-Anhydro-2',3'-O-isopropyliden-8-hydroxy-adenosin；2',3'-O-Isopropyliden-8,5'-anhydro-8-oxyadenosin
• CAS: 19210-11-8
• 化学式: C₁₃H₁₅N₅O₄
• 分子量: 305.293
• InChiKey: VBXVHMIFMIBOSY-YQYOSIFRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.22
• 重原子数：
  22.0
• 可旋转键数：
  0.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  106.54
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  2'-O,3'-O-isopropylidene-5'-O,8-cycloadenosine 在 单过氧邻苯二甲酸 作用下， 以 1,4-二氧六环 为溶剂， 生成 O^{2'_,O3'_{-isopropylidene-8,O}5'}-cyclo-adenosine 1-oxide
  参考文献：
  名称：

  Studies of nucleosides and nucleotides. LXVI. Purine cyclonucleosides. 29. N-oxides of adenine cyclonucleosides.

  摘要：

  通过使用单邻苯二甲酸进行氧化，合成了 8，2'-、8，3'- 和 8，5'-S-环腺苷酸的 N1-氧化物。2'- 或 3'-O - 三异丙基苯磺酰基-8-溴腺苷经 N1 原子氧化并与 NaSH 环化后得到 2'- 或 3'-S - 环核苷 N-氧化物，从而明确合成了这些 N-氧化物的结构。对于 5'-异构体，2', 3'-乙氧基亚甲基-5'-对甲基苯磺酰-8-溴腺苷经单邻苯二甲酸和 NaSH 连续处理后转化为 8-巯基 N1-氧化物。在二甲基甲酰胺中用乙酸钠进行环化，然后用乙酸去除乙氧基亚甲基，得到 8，5'-S-环腺苷酸 N1-氧化物。研究了这些 N-氧化物的紫外光谱和核磁共振光谱特性。

  DOI：

  10.1248/cpb.23.2534
• 作为产物：
  描述：

  2',3'-异丙叉腺苷 在 copper dichloride 作用下， 以 乙腈 为溶剂， 生成 2'-O,3'-O-isopropylidene-5'-O,8-cycloadenosine
  参考文献：
  名称：

  Facile conversion of N6-benzoyladenosines into 5'-chloro-5'-deoxy-8-hydroxyadenosines by a reaction with cupric chloride: A prominent substituent effect of the N6-benzoyl group.

  摘要：

  N6-苯甲酰基-2', 3'-O-异丙叉腺苷 (1) 轻松转化为 N6-苯甲酰基-5'-氯-5'-脱氧-8-羟基-2', 3'-O-异丙叉腺苷 (3)通过在乙腈中与氯化铜反应，为腺苷的化学修饰提供了一种新方法。这反映了N6-苯甲酰基对腺苷化学反应活性的显着取代作用。

  DOI：

  10.1248/cpb.39.1902

文献信息

• Reaction of nucleosides with lead tetra-acetate: facile formation of cyclonucleosides
  作者：Keiji Kameyama、Magoichi Sako、Kosaku Hirota、Yoshifumi Maki

  DOI：10.1039/c39840001658

  日期：——

  Reaction of appropriatel protected purine nucleosides (adenosine and guanosine) with lead tetra-acetate results in the formation of the corresponding 5′-O,8-cyclopurine nucleosides (2), whereas that of the protected pyrimidine nucleosides (uridine and cytidine) give predominantly 5-acetoxy-5′-O,6-cyclo-5,6-dihydrouridine(4).

  适当保护的嘌呤核苷（腺苷和鸟苷）与四乙酸铅的反应导致形成相应的5'- O，8-环嘌呤核苷（2），而受保护的嘧啶核苷（尿苷和胞苷）则主要产生5-乙酰氧基-5'- O，6-环-5,6-二氢尿苷（4）。
• Photochemical intramolecular cyclisation of purine and pyrimidine nucleosides induced by an electron acceptor
  作者：Magoichi Sako、Kaoru Shimada、Kosaku Hirota、Yoshifumi Maki

  DOI：10.1039/c39860001704

  日期：——

  Irradiation of appropriately protected purine nucleosides (guanosine and adenosine)(1) and cytidine (2a) in the presence of pyrimido[5,4-g]pteridine N-oxide (5) with u.v.–visible light results in the exclusive formation of the corresponding 5′-O,8-cyclopurine nucleosides (3) and 5′-O,6-cyclocytidine (4a).

  在存在嘧啶并[5,4- g ]哌啶N-氧化物（5）的情况下，用紫外可见光照射适当保护的嘌呤核苷（鸟苷和腺苷）（1）和胞苷（2a）会导致排泄物的排他性形成。相应的5'- O，8-环嘌呤核苷（3）和5'- O，6-环胞苷（4a）。
• Gani, David; Johnson, Alan W., Journal of the Chemical Society. Perkin transactions I, 1982, p. 1197 - 1204
  作者：Gani, David、Johnson, Alan W.

  DOI：——

  日期：——
• 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.
• Intramolecular Cyclization of Purine Nucleosides by N-Halogenosuccinimides/Acetic Acid. A Mechanistic Aspect on the C(8)-Halogenation of Purine Nucleosides
  作者：Yoshifumi Maki、Magoichi Sako、Takao Saito、Kosaku Hirota

  DOI：10.3987/com-87-4405

  日期：——