N⁶-benzoyl-5'-O,8-cyclo-2',3'-O-isopropylideneadenosine | 107855-22-1

• 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: N⁶-benzoyl-5'-O,8-cyclo-2',3'-O-isopropylideneadenosine
• 英文别名: N⁶-benzoyl-2',3'-O-isopropylidene-5-O'-cycloadenosine；N-[(1R,13R,14R,18R)-16,16-dimethyl-11,15,17,19-tetraoxa-2,4,6,9-tetrazapentacyclo[11.5.1.02,10.03,8.014,18]nonadeca-3,5,7,9-tetraen-7-yl]benzamide
• CAS: 107855-22-1
• 化学式: C₂₀H₁₉N₅O₅
• 分子量: 409.401
• InChiKey: NURQLKHVTVQIHY-XWXWGSFUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  30
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N⁶-benzoyl-5'-O,8-cyclo-2',3'-O-isopropylideneadenosine 生成 N6-苯甲酰基-2',3'-O-异丙亚基腺苷
  参考文献：
  名称：

  SAKO, MAGOICHI;SAITO, TAKAO;KAMEYAMA, KEIJI;HIROTA, KOSAKU;MAKI, YOSHIFUM+, J. CHEM. SOC. CHEM. COMMUN.,(1987) N 17, 1298-1299

  摘要：

  DOI：
• 作为产物：
  描述：

  N6-苯甲酰基-2',3'-O-异丙亚基腺苷 在 四氰基乙烯 作用下， 以 乙腈 为溶剂， 反应 9.0h， 生成 N⁶-benzoyl-5'-O,8-cyclo-2',3'-O-isopropylideneadenosine
  参考文献：
  名称：

  6-苯甲酰腺苷衍生物的氧化光环化。容易形成喹唑啉嘌呤环系统

  摘要：

  在氧化剂的存在下辐照2'，3'，5'-三-乙酰基-6-苯甲酰基腺苷衍生物1导致一种新型的氧化光环化反应，导致8-（2'，3'，5' -三-乙酰基-β--呋喃呋喃糖基）喹唑啉基[2,1- ]嘌呤-12-衍生物2。

  DOI：

  10.1016/s0040-4039(00)95687-9

文献信息

• 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）。
• 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.
  作者：Yukio KITADE、Ryuji NAKANISHI、Magoichi SAKO、Kosaku HIROTA、Yoshifumi MAKI

  DOI：10.1248/cpb.39.1902

  日期：——

  Facile conversion of N6-benzoyl-2', 3'-O-isopropylideneadenosine (1) into N6-benzoyl-5'-chloro-5'-deoxy-8-hydroxy-2', 3'-O-isopropylideneadenosine (3) by a reaction with cupric chloride in acetonitrile provides a new method for the chemical modification of adenosines. This reflects the prominent substitutent effect of N6-benzoyl group on the chemical reactivity of adenosines.

  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。
• Reductive cleavage of the O–C(8) bond in 5′-O,8-cycloadenosines. Intramolecular protection of the 8-position and the 5′-hydroxy group in adenosines
  作者：Magoichi Sako、Takao Saito、Keiji Kameyama、Kosaku Hirota、Yoshifumi Maki

  DOI：10.1039/c39870001298

  日期：——

  Upon treatment with NaBH3CN in acetic acid at ambient temperature, N6-acyl-5′-O,8-cycloadenosines (1) with or without carbon functional groups on the 2-position undergo exclusively a reductive O–C(8) bond cleavage to give the corresponding N6-acyladenosines (2).

  在室温下用乙酸中的NaBH 3 CN处理后，在2位上带有或不带有碳官能团的N 6-酰基-5' - O，8-环腺苷（1）仅经历还原性的O-C（8）键裂解得到相应的N 6-酰基腺苷（2）。
• 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：——