3'-O-allyl-2,6-diaminopurine riboside | 212061-36-4

• 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: 3'-O-allyl-2,6-diaminopurine riboside
• 英文别名: (2R,3R,4S,5R)-2-(2,6-diaminopurin-9-yl)-5-(hydroxymethyl)-4-prop-2-enoxyoxolan-3-ol
• CAS: 212061-36-4
• 化学式: C₁₃H₁₈N₆O₄
• 分子量: 322.324
• InChiKey: QPBDKAJQTRKPEJ-WOUKDFQISA-N

物化性质

• 沸点：
  731.9±70.0 °C(Predicted)
• 密度：
  1.77±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  155
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  3-溴丙烯 、 2-氨基腺嘌呤核苷 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 生成 3'-O-allyl-2,6-diaminopurine riboside
  参考文献：
  名称：

  2'-O-aminooxy-modified oligonucleotides

  摘要：

  提供含有氨氧基团的核苷酸组成。根据优选实施例，提供了可以与所选的RNA或DNA序列特异杂交的寡核苷酸和寡核苷酸类似物，其中寡核苷酸的核苷酸基团至少有一个被修改以包括氨氧基团。

  公开号：

  US06127533A1

文献信息

• Synthesis of 2‘-<i>O</i>-[2-[(<i>N,N</i>-Dimethylamino)oxy]ethyl] Modified Nucleosides and Oligonucleotides
  作者：Thazha P. Prakash、Andrew M. Kawasaki、Allister S. Fraser、Guillermo Vasquez、Muthiah Manoharan

  DOI：10.1021/jo0103975

  日期：2002.1.1

  route has been developed for the synthesis of 2'-O-[2-[(N,N-dimethylamino)oxy]ethyl] (abbreviated as 2'-O-DMAOE) modified purine and pyrimidine nucleosides and their corresponding nucleoside phosphoramidites and solid supports. To synthesize 2'-O-DMAOE purine nucleosides, the key intermediate B (Scheme 1) was obtained from the 2'-O-allyl purine nucleosides (13a and 15) via oxidative cleavage of the carbon-carbon

  已开发出一种通用的合成路线，用于合成2'-O- [2-[（N，N-二甲基氨基）氧基]乙基]（缩写为2'-O-DMAOE）修饰的嘌呤和嘧啶核苷及其相应的核苷亚磷酰胺和固体支持物。为了合成2'-O-DMAOE嘌呤核苷，通过将碳-碳键氧化裂解为相应的醛，从2'-O-烯丙基嘌呤核苷（13a和15）获得关键中间体B（方案1）通过减少。为了合成嘧啶核苷，用乙二醇的硼酸酯打开2,2'-脱水-5-甲基尿苷5，得到了关键的中间体B。将2'-O-（2-羟乙基）核苷进行了高产率的转化，通过区域选择性的Mitsunobu反应，形成相应的2'-O- [2-[（1,3-dihydro-1，3-二氧代-2H-异吲哚-2-基）氧基]乙基]核苷（18、19和20）。随后将这些化合物脱保护并转化为2'-O- [2-[（[亚甲基氨基）氧基]乙基]衍生物（22、23和24）。还原并用甲醛进行第二次还原胺化，得到相应的2'-O-
• Oligonucleotide analogs having modified dimers
  申请人：ISIS Pharmaceuticals, Inc.

  公开号：US06420549B1

  公开（公告）日：2002-07-16

  Modified dimers having a ribose sugar moiety in the 5′ nucleoside and a 2′ modified sugar in the 3′ nucleoside are provided. The modified dimers are useful in the preparation of oligonucleotide analogs having enhanced properties compared to native oligonucleotides, including increased nuclease resistance, enhanced binding affinity and improved protein binding.

  提供具有核糖糖基在5'核苷和3'核苷中具有2'修饰糖的改性二聚体。这些改性二聚体在制备寡核苷酸类似物方面非常有用，相比于天然寡核苷酸，具有增强性能，包括增加核酸酶抗性、增强结合亲和力和改善蛋白结合。
• Aminooxy-modified nucleosidic compounds and oligomeric compounds prepared therefrom
  申请人：ISIS Pharmaceuticals, Inc.

  公开号：US06639062B2

  公开（公告）日：2003-10-28

  Nucleosidic monomers and oligomeric compounds prepared therefrom are provided which have increased nuclease resistance, substituent groups (such as 2′-aminooxy groups) for increasing binding affinity to complementary strand, and regions of 2′-deoxy-erythro-pentofuranosyl nucleotides that activate RNase H. Such oligomeric compounds are useful for diagnostics and other research purposes, for modulating the expression of a protein in organisms, and for the diagnosis, detection and treatment of other conditions susceptible to oligonucleotide therapeutics.

  提供了由核苷酸单体和寡聚物制备的具有增强核酸酶抗性的化合物，这些化合物具有取代基团（如2'-氨氧基团）以增加与互补链的结合亲和力，并具有激活RNase H的2'-去氧-赤霉醇-核苷酸区域。这种寡聚物化合物可用于诊断和其他研究目的，用于调节生物体中蛋白质的表达，并用于对其他易受寡核苷酸治疗影响的疾病进行诊断、检测和治疗。
• AMINOOXY-MODIFIED NUCLEOSIDIC COMPOUNDS AND OLIGOMERIC COMPOUNDS PREPARED THEREFROM
  申请人：——

  公开号：US20030088079A1

  公开（公告）日：2003-05-08

  Nucleosidic monomers and oligomeric compounds prepared therefrom are provided which have increased nuclease resistance, substituent groups (such as 2′-aminooxy groups) for increasing binding affinity to complementary strand, and regions of 2′-deoxy-erythro-pentofuranosyl nucleotides that activate RNase H. Such oligomeric compounds are useful for diagnostics and other research purposes, for modulating the expression of a protein in organisms, and for the diagnosis, detection and treatment of other conditions susceptible to oligonucleotide therapeutics.

  提供具有增强核酸酶抵抗性的核苷酸单体和由此制备的寡聚化合物，这些化合物具有取代基团（例如2'-氨氧基基团）以增加与互补链的结合亲和力，并具有激活RNase H的2'-脱氧-赤霉糖核苷酸区域。这些寡聚化合物可用于诊断和其他研究目的，用于调节生物体中蛋白质的表达，并用于对易受寡核苷酸治疗的其他疾病进行诊断、检测和治疗。
• NOVEL 2'-O-ALKYL NUCLEOSIDES AND PHOSPHORAMIDITES PROCESSES FOR THE PREPARATION AND USES THEREOF
  申请人：ISIS PHARMACEUTICALS, INC.

  公开号：EP0651759A1

  公开（公告）日：1995-05-10