N⁶,N⁶-dibenzoyldeoxyadenosine | 6711-37-1

• 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: N⁶,N⁶-dibenzoyldeoxyadenosine
• 英文别名: 6-N,N-dibenzoyl-2'-deoxyadenosine；N,N-Dibenzoyl-2'-deoxyadenosine；N-benzoyl-N-[9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]purin-6-yl]benzamide
• CAS: 6711-37-1
• 化学式: C₂₄H₂₁N₅O₅
• 分子量: 459.461
• InChiKey: WLTBUTVYURQDEF-IPMKNSEASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  34
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  131
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N⁶,N⁶-dibenzoyldeoxyadenosine 在 2,4-二磺酰氯基均三甲苯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.34h， 生成 N-benzoyl-N-[9-[(2R,4S,5R)-4-bis(phenylsulfanyl)phosphoryloxy-5-[[[3-(imidazol-1-ylmethyl)phenyl]-bis(4-methoxyphenyl)methoxy]methyl]oxolan-2-yl]purin-6-yl]benzamide
  参考文献：
  名称：

  3-(Imidazol-1-ylmethyl)-4',4"-dimethoxytrityl: a new functionalized 5'-hydroxyl protecting group capable of rapid internucleotidic bond formation in the phosphorothio ester approach

  摘要：

  DOI：

  10.1021/jo00381a047
• 作为产物：
  描述：

  2'-脱氧腺苷 在 吡啶 、 碳酸氢钠 作用下， 反应 6.25h， 生成 N⁶,N⁶-dibenzoyldeoxyadenosine
  参考文献：
  名称：

  Transient protection: efficient one-flask syntheses of protected deoxynucleosides

  摘要：

  DOI：

  10.1021/ja00369a029

文献信息

• SELECTIVE REMOVAL OF TERMINAL DIMETHOXYTRITYL GROUPS
  作者：Hiroshi Takaku、Kazuhiro Morita、Takashi Sumiuchi

  DOI：10.1246/cl.1983.1661

  日期：1983.11.5

  N6’N6,3′,5′-O-Protected deoxyadenosine derivatives were found to be key intermediate for synthesis of oligodeoxyribonucleotides. Treatment of protected deoxyadenosine derivatives with 3% trichloroacetic acid in nitromethane-methanol (95:5) gave the corresponding de-dimethoxytritylated deoxyadenosine derivatives without causing any damage to the glycosidic bond.

  N6'N6,3',5'-O-保护的脱氧腺苷衍生物被发现是合成寡脱氧核糖核苷酸的关键中间体。用3%三氯乙酸的硝基甲烷-甲醇(95:5)溶液处理受保护的脱氧腺苷衍生物，得到相应的脱二甲氧基三苯甲基化的脱氧腺苷衍生物，且不会对糖苷键造成任何损害。
• The effect of protecting groups of the nucleobase and the sugar moieties on the acidic hydrolysis of the glycosidic bond of 2deoxyadenosine: a kinet
  作者：Gerald Remaud、Xiao-Xiong Zhou、Jyoti Chattopadhyaya、Mikko Oivanen、Harri Lönnberg

  DOI：10.1016/s0040-4020(01)90322-9

  日期：1987.1

  The rate constants for the hydrolysis of several 6 -substituted 2deoxyadenosines were measured at different concentrations of oxonium ion in order to assess the role of various 6 and sugar protecting groups in depurination reaction encountered in nucleic acid synthesis. The site of protonation was established by recording the 15N NMR spectra in DMSO-6 both in the absence and presence of trifluoroacetic

  在不同浓度的氧鎓离子下，测量了几种6-取代的2个脱氧腺苷的水解速率常数，以评估各种6-和糖保护基在核酸合成中遇到的脱嘌呤反应中的作用。通过在不存在和存在三氟乙酸的情况下在DMSO- 6中记录15 N NMR光谱来确定质子化的位点。6-酰基-2脱氧腺苷的单阳离子的异常不稳定性是由优选的7个质子化引起的。
• A New Method for Removal of Modified Trityl and Pixyl Groups by Use of an Acid Species Generated by Reaction of Diethyl Oxomalonate with Methanol
  作者：Mitsuo Sekine

  DOI：10.1080/15257779408012160

  日期：1994.7

  Diethyl oxomalonate (DEOM) was found to exhibit unique properties as a new type of detritylating reagent in the presence of methanol. A variety of deoxyribonucleoside derivatives protected with modified trityl groups were allowed to react with DEOM. The ease of detritylation highly depended on the basicity of protected bases of adenine, guanine and cytosine. Inhibitory effects of various amines possessing the pKa values between 0.79-10.87 on the present detritylation were studied. Several mechanistic considerations were alsb discussed on the basis of H-1 and C-13 NMR studies of the DEOM-Methanol adduct.
• Ribosylation of Pyrimidine 2′-Deoxynucleosides
  作者：Sergey N. Mikhailov、Erik De Clercq、Piet Herdewijn

  DOI：10.1080/07328319608002433

  日期：1996.7

  The previously developed method for the preparation of 2'-O-D-ribofuranosyl-nucleosides is extended to ribosylation of 2'-deoxynucleosides. The scope and limitations of this reaction are discussed.
• SEKINE, MITSUO;NARUI, SHIN-ICHIRO;HATA, TSUJIAKI, 7TH SYMP. CHEM. NUCL. ACID COMPON., BECHYNE CASTLE, AUG. 30TH - SEPT. 5TH+
  作者：SEKINE, MITSUO、NARUI, SHIN-ICHIRO、HATA, TSUJIAKI

  DOI：——

  日期：——