2-异丁酰胺基鸟苷2’,3’,5’-三(异丁酸酯) | 70337-80-3

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 中文名称: 2-异丁酰胺基鸟苷2’,3’,5’-三(异丁酸酯)
• 英文名称: N²,2',3',5'-tetraisobutyrylguanosine
• 英文别名: [(2R,3R,4R,5R)-5-[2-(2-methylpropanoylamino)-6-oxo-1H-purin-9-yl]-3,4-bis(2-methylpropanoyloxy)oxolan-2-yl]methyl 2-methylpropanoate
• CAS: 70337-80-3
• 化学式: C₂₆H₃₇N₅O₉
• 分子量: 563.608
• InChiKey: DDEJRIIPKABPRC-UVLLPENVSA-N

物化性质

• 溶解度：
  可溶于氯仿、DMSO、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  40
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  177
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  2-异丁酰胺基鸟苷2’,3’,5’-三(异丁酸酯) 在 sodium hydroxide 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 96.0h， 生成 O6-苄基鸟苷
  参考文献：
  名称：

  N2,3-etheno-2'-deoxyguanosine [8,9-dihydro-9-oxo-2'-deoxy-3-.beta.-D-ribofuranosylimidazo[2,1-b]purine]: a practical synthesis and characterization

  摘要：

  The literature methods for the syntheses of N2,3-etheno-2'-deoxyguanosine (1a) and its 5'-O-phosphate are associated with very low overall yields. We now describe a route starting in the riboside series that permits the production of 1a in practical quantities and has allowed its complete chemical characterization for the first time. O6-Benzylguanosine (6b) when treated with bromoacetaldehyde under conditions of continuous buffering gives the N2,3-etheno derivative 7b in 48% yield. The 3',5'-O-(1,1,3,3-tetraisopropyldisiloxa-1,3-diyl) derivative (8b, 89 % yield) of 7b when allowed to react with phenyl chlorothionoformate led to the corresponding 2' ester (10,50%). 2'-Deoxygenation of 10 by the Barton procedure then afforded 65% of 11, and deprotection of the latter (Bu4N+F-) gave 12 quantitatively. Catalytic hydrogenation of 12 then produced pure la in 86% yield. Stability studies on la have confirmed its exquisite sensitivity to acid and demonstrated its relative stability to alkali and the other reagents used in automated DNA synthesis (phosphoramidate method).

  DOI：

  10.1021/jo00061a033
• 作为产物：
  描述：

  N²,2',3',5'-tetraisobutyryl-O⁶-p-nitrophenylethylguanosine 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 吡啶 为溶剂， 反应 3.0h， 以81%的产率得到2-异丁酰胺基鸟苷2’,3’,5’-三(异丁酸酯)
  参考文献：
  名称：

  的p -nitrophenylethyl（NPE）组：一种多功能的新的保护基团为磷酸和核苷和核苷酸糖苷配基保护

  摘要：

  描述了用于合成寡核苷酸的新的单体结构单元的合成，该新的单体结构单元通过磷酸三酯方法进行合成，该方法包含对-硝基苯基乙基用于磷酸盐和糖苷配基的保护。在澳在鸟苷的酰胺官能团的阻断6可以通过Mitsunobu反应形成对应的O来实现6 - p -nitrophenylethyl衍生物（4，5，10）。糖保护胸苷（16）和尿苷（17）已经被在澳烷基化4以S Ñ 1型反应通过p在苯，以形成将O碳酸盐-nitrophenylethyl碘化银4 - p -nitrophenylethyl衍生物（18，19）。在-2'-脱氧胞苷（氨基的保护25）和胞苷（26）可以通过1-（直接进行p -nitrophenylethoxycarbonyl） -苯并三唑的DMF，得到相应的氨基甲酸酯（27，28）作为一种新的类型为N 4-酰化胞苷衍生物。p 2'-脱氧腺苷（33）和腺苷（34）中氨基的硝基苯基乙氧基羰基化作用需

  DOI：

  10.1016/0040-4020(84)85103-0

文献信息

• Regioselective protection of carbohydrate derivatives.
  作者：Shigeyoshi Nishino、Hatsuko Takamura、Yoshiharu Ishido

  DOI：10.1016/s0040-4020(01)87616-x

  日期：1986.1

  A simple treatment of fully aroylated purine and pyrimidine ribo-nucleosides with pulverized potassium tert-butoxide in tetrahydrofuran (THF) or dichloromethane under a controlled condition gave a mixture of the corresponding di-O-aroyl derivatives in which 2'-OH derivatives are preponderant over 3'-OH derivatives; 3',5'-di-O-benzoyluridine, N4, 3', 5'-tribenzoylcytidine, N4, 3', 5'-tri-o-toluoylcytidine

  在控制条件下，在四氢呋喃（THF）或二氯甲烷中，用粉碎的叔丁醇钾简单地处理完全芳基化的嘌呤和嘧啶核糖核苷，得到相应的二-O-芳酰基衍生物的混合物，其中2'-OH衍生物占优势超过3'-OH衍生物；3' ，5'-二-O- benzoyluridine，N 4，3' ，5'-tribenzoylcytidine，N 4，3' ，5'-三-邻- toluoylcytidine，N 2，3' ，5'-tribenzoylguanosine，和获得N 2-异丁酰基-3'，5'-二-O-苯甲酰基鸟苷结晶，产率分别为80％，78％，72％，67％和65％。
• Partial protection of carbohydrate derivatives. part 18. simple, preparative procedure for 5'--acylribonucleosides; highly regioselective -deacylation at 2' and 3' positions of fully acylated purine and pyrimidine ribonucleoside through sodium methoxide-thf system
  作者：Shigeyoshi Nishino、Md.Azizur Rahman、Hatsuko Takamura、Yoshiharu Ishido

  DOI：10.1016/s0040-4020(01)91350-x

  日期：1985.1

  A treatment of fully acylated purine and pyrimidine ribonucleosides with a small excess amount of sodium methoxide in THF at room temperature gave the corresponding 5'-acylates in excellent yields; N-acyl groups on the nucleic acid base moieties of adenosine and cytidine in addition to guanosine derivatives satisfactorily survived under the conditions used.

  在室温下用少量过量的甲醇钠在THF中处理完全酰化的嘌呤和嘧啶核糖核苷，得到的相应5'-酰化物收率很好；除鸟苷衍生物外，腺苷和胞苷的核酸碱基部分上的N-酰基在所使用的条件下令人满意地存活。
• Biosynthetic Production of [<i>N</i>²,1,3,7,9-¹⁵N]Guanosine and [1,3,7,9-¹⁵N]inosine and conversion into [<i>N</i>⁶,1,3,7,9-¹⁵N]adenosine for structure elucidation of RNA by heteronuclear NMR
  作者：Annette C. Niemann、Mónica Meyer、Thomas Engeloch、Oliver Botta、Alfons Hädener、Peter Strazewski

  DOI：10.1002/hlca.19950780213

  日期：1995.3.22

  A procedure was developed for the biosynthetic preparation of 15N-labelled guanosine and inosine through the action of a mutant Bacillus subtilis strain. Crude [N2,1,3,7,9-15N]guanosine and [1,3,7,9-15N]inosine were isolated from the culture filtrate by precipitation and anion-exchange chromatography (Scheme 1). No cell lysis and no enzymatic degradation was necessary. The per-isobutyrylated derivatives

  通过突变枯草芽孢杆菌菌株的作用，开发了一种生物合成制备15 N标记的鸟苷和肌苷的程序。粗[ Ñ 2，1,3,7,9- 15 N]鸟苷和[1,3,7,9- 15 N]肌苷从通过沉淀和阴离子交换层析（培养滤液中分离方案1）。无需细胞裂解，也无需酶促降解。全异丁酰化衍生物1和2从复杂的混合物中分离纯化产物，通过不同的亲脂性对其进行纯化，然后分三步进行分离，包括正相和反相硅胶色谱法。一升复杂的营养培养基可产生8.44 mmol的鸟苷衍生物和2.84 mmol的肌苷衍生物，平均富集15 N较高（分别为83.5和91.9原子％）。[ Ñ 6，1,3,7,9- 15 N]腺苷（4）从得到的2'，3'，5'-三ö异丁酰基[1,3,7,9- 15 N]肌苷（1）通过将其1,2,4-三唑基衍生物与15 NH 3水溶液氨解（方案2）。
• Synthesis, oligonucleotide incorporation and base pair stability of 7-methyl-8-oxo-2′-deoxyguanosine
  作者：Michelle L. Hamm、Kelly Billig

  DOI：10.1039/b612597b

  日期：——

  7-Methyl-8-oxo-2′-deoxyguanosine, an analogue of the abundant promutagen 8-oxo-2′-deoxyguanosine, was incorporated into oligonucleotides and tested for its stability in various base pairs.

  将 7-甲基-8-氧代-2â²-脱氧鸟苷（一种丰富的原 8-氧代-2â²-脱氧鸟苷的类似物）加入寡核苷酸中，并测试其在各种碱基对中的稳定性。
• Flockerzi, Dieter; Silber, Gunter; Charubala, Ramamurthy, Liebigs Annalen der Chemie, 1981, # 9, p. 1568 - 1585
  作者：Flockerzi, Dieter、Silber, Gunter、Charubala, Ramamurthy、Schlosser, Wilhelm、Varma, Rajendra Singh、et al.

  DOI：——

  日期：——