N-(9-((2R,4S,5R)-4-(bis(4-methoxyphenyl)(phenyl)methoxy)-5-(hydroxymethyl)tetrahydrofuran-2-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl)isobutyramide | 140712-81-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: N-(9-((2R,4S,5R)-4-(bis(4-methoxyphenyl)(phenyl)methoxy)-5-(hydroxymethyl)tetrahydrofuran-2-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl)isobutyramide
• 英文别名: N2-isobutyryl-3'-O-(4,4'-dimethoxytrityl)-2'-deoxyguanosine；N-[9-[(2R,4S,5R)-4-[bis(4-methoxyphenyl)-phenylmethoxy]-5-(hydroxymethyl)oxolan-2-yl]-6-oxo-1H-purin-2-yl]-2-methylpropanamide
• CAS: 140712-81-8
• 化学式: C₃₅H₃₇N₅O₇
• 分子量: 639.708
• InChiKey: FRMKNQDKTCCNED-ZGIBFIJWSA-N

物化性质

• 熔点：
  109-110 °C
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  47
• 可旋转键数：
  11
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  146
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  N-(9-((2R,4S,5R)-4-(bis(4-methoxyphenyl)(phenyl)methoxy)-5-(hydroxymethyl)tetrahydrofuran-2-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl)isobutyramide 在 N-甲基吗啉 、 1H-1,2,4-三唑 、 三氯化磷 作用下， 以 二氯甲烷 为溶剂， 以56%的产率得到
  参考文献：
  名称：

  Synthesis of 3′-Azido-3′-Deoxythymidine-Terminated Oligonucleotide

  摘要：

  A method of completely chemical synthesis of 3'-azido-3'-deoxythymidine-terminated oligonucleotides via 5'-H-phosphonate of AZT is described.

  DOI：

  10.1080/07328319808004703
• 作为产物：
  描述：

  4,4'-双甲氧基三苯甲基氯 在 吡啶 、 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 21.5h， 生成 N-(9-((2R,4S,5R)-4-(bis(4-methoxyphenyl)(phenyl)methoxy)-5-(hydroxymethyl)tetrahydrofuran-2-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl)isobutyramide
  参考文献：
  名称：

  TAU-TARGETING OLIGONUCLEOTIDE GAPMERS

  摘要：

  提供了反义寡核苷酸。这些反义寡核苷酸在制备gapmers以抑制Tau mRNA转录方面非常有用。抑制Tau mRNA转录可能导致受试者Tau蛋白质量的降低，从而治疗与Tau表达有关的疾病和疾病，包括阿尔茨海默病和原发性Tau病。

  公开号：

  US20220195437A1

文献信息

• Novel Chemoenzymatic Protocol for the Synthesis of 3‘-<i>O</i>-Dimethoxytrityl-2‘-deoxynucleoside Derivatives as Building Blocks for Oligonucleotide Synthesis
  作者：Alba Díaz-Rodríguez、Susana Fernández、Yogesh S. Sanghvi、Miguel Ferrero、Vicente Gotor

  DOI：10.1021/op050253i

  日期：2006.5.1

  An easy, efficient, and scalable chemoenzymatic strategy for the synthesis of 3‘-O-dimethoxytrityl-2‘-deoxynucleosides has been developed. A key feature of this approach is the regioselective synthesis of 5‘-O-levulinyl-2‘-deoxynucleosides through enzymatic acylation in the presence of Candida antarctica lipase B. In addition, it was observed that the deblocking of levulinyl group from the 5‘-position

  已经开发了用于合成3' - O-二甲氧基三苯甲基-2'-脱氧核苷的简单，有效且可扩展的化学酶策略。该方法的关键特征是在南极假丝酵母脂肪酶B存在下，通过酶促酰化反应进行5'- O-乙酰丙氨酰-2'-脱氧核苷的区域选择性合成。此外，还观察到乙酰丙氨酰基从5'解封位置与常规的碱保护基完全相容。为了证明该方法的可扩展性，以25 g规模合成了3'- O-二甲氧基三苯甲基胸苷（4a）。这些单体（4 a - d）是合成寡核苷酸的有用组成部分。
• Methyl 4-toluenesulfonyloxymethylphosphonate, a new and versatile reagent for the convenient synthesis of phosphonate-containing compounds
  作者：Ivana Kóšiová、Zdeněk Točík、Miloš Buděšínský、Ondřej Šimák、Radek Liboska、Dominik Rejman、Ondřej Pačes、Ivan Rosenberg

  DOI：10.1016/j.tetlet.2009.09.062

  日期：2009.12

  A straightforward procedure leading to the new phosphonylating reagent, methyl 4-toluenesulfonyloxymethylphosphonate, requiring no chromatographic purification is described. This stable reagent works with the same efficiency as dimethyl and other dialkyl esters for the introduction of an O-phosphonomethyl moiety while, in contrast to dimethyl ester, it does not cause any unwanted methylation of sensitive

  描述了一种无需新的色谱纯化方法即可直接产生新的膦酰化试剂4-甲苯磺酰氧基甲基膦酸甲酯的方法。对于引入O-膦酰基甲基部分，该稳定的试剂与二甲基和其他二烷基酯具有相同的效率，而与二甲基酯相反，它不会引起敏感官能团的任何不希望的甲基化。举例说明了其以高产率用于被保护的核苷的烷基化的效用。
• Method for purifying 5' -protected 2' -deoxypurine nucleosides
  申请人：——

  公开号：US20030009028A1

  公开（公告）日：2003-01-09

  A method for efficiently purifying 5′ protected 2′-deoxypurine nucleosides, efficient production of which has previously been difficult. Impurities can be separated by obtaining the 5′ protected 2′-deoxypurine nucleoside as an inclusion crystal including a solvent such as that having a nitrile structure in order to purify the 5′ protected 2′-deoxypurine nucleoside at a high purity. This invention enables synthesis of highly purified protected deoxypurine nucleosides easily on a large scale, which has previously been performed by column chromatography method.

  一种用于高效纯化5′保护的2′-去氧嘌呤核苷的方法，先前其高效生产曾经困难。通过获得含有类似腈结构的溶剂的包含晶体，可将杂质分离以纯化5′保护的2′-去氧嘌呤核苷。该发明使得在大规模上轻松合成高纯度的保护去氧嘌呤核苷成为可能，而此前通常通过柱层析法进行。
• Method for purifying 5′-protected 2′-deoxypurine nucleosides
  申请人：Komatsu Hironori

  公开号：US06958391B2

  公开（公告）日：2005-10-25

  A method for efficiently purifying 5′ protected 2′-deoxypurine nucleosides, efficient production of which has previously been difficult. Impurities can be separated by obtaining the 5′ protected 2′-deoxypurine nucleoside as an inclusion crystal including a solvent such as that having a nitrile structure in order to purify the 5′ protected 2′-deoxypurine nucleoside at a high purity. This invention enables synthesis of highly purified protected deoxypurine nucleosides easily on a large scale, which has previously been performed by column chromatography method.

  一种高效纯化5'保护的2'-脱氧嘌呤核苷的方法，其高效生产先前曾经困难。通过获得包括具有腈结构的溶剂的包含晶体，可以分离杂质，以便高纯度地纯化5'保护的2'-脱氧嘌呤核苷。这项发明使得高纯度保护的脱氧嘌呤核苷易于大规模合成，这先前是通过柱层析法进行的。
• Method for purifying 5'-protected 2'-deoxypurine nucleosides
  申请人：Mitsui Chemicals, Inc.

  公开号：EP1253154B1

  公开（公告）日：2009-09-02