2'-deoxy-3',5'-di-O-(4-methylbenzoyl)adenosine | 121409-45-8

• 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: 2'-deoxy-3',5'-di-O-(4-methylbenzoyl)adenosine
• 英文别名: [(2R,3S,5R)-5-(6-aminopurin-9-yl)-3-(4-methylbenzoyl)oxyoxolan-2-yl]methyl 4-methylbenzoate
• CAS: 121409-45-8
• 化学式: C₂₆H₂₅N₅O₅
• 分子量: 487.515
• InChiKey: LFLNLGUAFCWMRQ-PWRODBHTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  36
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  131
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2'-deoxy-3',5'-di-O-(4-methylbenzoyl)adenosine 在 bis(1,5-cyclooctadiene)nickel (0) potassium phosphate 、 亚硝酸特丁酯 、 1,3-bis(2,6-diisopropylphenyl)imidazolidin-2-ylidene hydrochloride 、 氟化氢吡啶 作用下， 以 四氢呋喃 为溶剂， 反应 3.25h， 生成 9-[2-deoxy-3,5-di-O-(4-methylbenzoyl)-β-D-erythro-pentofuranosyl]-6-(4-methylphenyl)purine
  参考文献：
  名称：

  Fluoro, Alkylsulfanyl, and Alkylsulfonyl Leaving Groups in Suzuki Cross-Coupling Reactions of Purine 2‘-Deoxynucleosides and Nucleosides

  摘要：

  [GRAPHICS]Protected 2'-deoxynucleoside and nucleoside derivatives of 6-fluoropurine, 6-(3-methylbutyl)sulfanylpurine, and 6-(3-methylbutyl)ylsulfonyipurine undergo nickel- or palladium-mediated C-C cross-coupling with arylboronic acids to give good yields of 6-arylpurine products.

  DOI：

  10.1021/ol050063s
• 作为产物：
  描述：

  4-甲基苯甲酸酐 在 吡啶 作用下， 以 甲醇 为溶剂， 反应 14.0h， 生成 2'-deoxy-3',5'-di-O-(4-methylbenzoyl)adenosine
  参考文献：
  名称：

  Nucleic Acid Related Compounds. 127. Selective N-Deacylation of N,O-Peracylated Nucleosides in Superheated Methanol¹

  摘要：

  Solutions of peracylated adenosine, cytidine, and related nucleoside derivatives undergo selective N-deacylation upon heating at elevated temperatures (oil bath >= 105 degrees C) in methanol. An increase in the bulk of the N-acyl group has little effect on the rate of N-deacylation but increases the N/O selectivity ratio. Extended heating is required for N-deacylation with arylcarboxylic acid derivatives. Contamination with acidic or basic reagent residues is avoided.

  DOI：

  10.1021/jo051256w

文献信息

• The Synthesis of 2′-Deoxyadenosine<i>via</i>Stereospecific Coupling Reaction
  作者：Hiroshi Kawakami、Hajime Matsushita、Yoshitake Naoi、Kazuo Itoh、Hajime Yoshikoshi

  DOI：10.1246/cl.1989.235

  日期：1989.2

  The coupling reaction of the sodium salt of adenine, which could be easily prepared by deprotonation with sodium hydroxide or sodium methoxide, with 1-α-chloro-2-deoxyribose derivative proceeded in a good stereospecific manner in acetone as a solvent to give the β-anomer of the corresponding acylated adenosine.

  腺嘌呤的钠盐（可以通过用氢氧化钠或甲醇钠去质子化轻松制备）与1-α-氯-2-脱氧核糖衍生物的偶联反应在丙酮作为溶剂中以良好的立体定向方式进行，得到β相应酰化腺苷的端基异构体。
• Process for preparing 2'-deoxy-beta-adenosine
  申请人：Japan Tobacco Inc.

  公开号：EP0350292A2

  公开（公告）日：1990-01-10

  2′-deoxy-β-adenosine can be easily obtained industrially without using expensive or dangerous materials by the process of the present invention, which comprises the steps of: allowing an adenine salt to condense with a hydroxyl protected derivative of pentofuranose to produce a hydroxyl protected derivative of adenine, and then eliminating the protecting groups.

  2′-脱氧-β-腺苷可以通过本发明的工艺在不使用昂贵或危险材料的情况下轻松地工业化获得，该工艺包括以下步骤：使腺嘌呤盐与戊呋喃糖的羟基保护衍生物缩合，生成腺嘌呤的羟基保护衍生物，然后消除保护基团。
• Oligonucleotide Synthesis Involving Deprotection of Amidine-Type Protecting Groups for Nucleobases under Acidic Conditions
  作者：Akihiro Ohkubo、Yasukazu Kuwayama、Yudai Nishino、Hirosuke Tsunoda、Kohji Seio、Mitsuo Sekine

  DOI：10.1021/ol100676j

  日期：2010.6.4

  Amidine-type protecting groups, i.e., N,N-dimethylformamidine (dmf) and N,N-dibutylformamidine (dbf) groups, introduced Into nucleobases were rapidly removed under mild acidic conditions using imidazolium triflate (IMT) or 1-hydroxybenztriazole (HOBt). This new deprotection strategy allowed a 2'-O-methyl-RNA derivative bearing a base-labile group to be efficiently synthesized using a silyl-type linker. It was also found that our new method could be applied to the synthesis of an unmodified RNA oligomer.
• US5262531A
  申请人：——

  公开号：US5262531A

  公开（公告）日：1993-11-16
• Nucleic Acid Related Compounds. 127. Selective N-Deacylation of N,O-Peracylated Nucleosides in Superheated Methanol¹
  作者：Ireneusz Nowak、Martin Conda-Sheridan、Morris J. Robins

  DOI：10.1021/jo051256w

  日期：2005.9.1

  Solutions of peracylated adenosine, cytidine, and related nucleoside derivatives undergo selective N-deacylation upon heating at elevated temperatures (oil bath >= 105 degrees C) in methanol. An increase in the bulk of the N-acyl group has little effect on the rate of N-deacylation but increases the N/O selectivity ratio. Extended heating is required for N-deacylation with arylcarboxylic acid derivatives. Contamination with acidic or basic reagent residues is avoided.