5'-O-(4,4'-dimethoxytrityl)-3'-O-levulinoyl-thymidine | 93134-37-3

• 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: 5'-O-(4,4'-dimethoxytrityl)-3'-O-levulinoyl-thymidine
• 英文别名: levulinoyl(-3)[DMT(-5)]2-deoxy-D-eryPenf(b)-thymin-1-yl；[(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] 4-oxopentanoate
• CAS: 93134-37-3
• 化学式: C₃₆H₃₈N₂O₉
• 分子量: 642.706
• InChiKey: OMGXBEJASAIXAA-DCMFLLSESA-N

物化性质

• 熔点：
  88-92 °C
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  47
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  130
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  5'-O-(4,4'-dimethoxytrityl)-3'-O-levulinoyl-thymidine 在 cesium fluoride N-甲基咪唑 、 triisopropylbenzenesulfonyl chloride 作用下， 以 吡啶 、 水 、 溶剂黄146 、 乙腈 为溶剂， 反应 2.33h， 生成
  参考文献：
  名称：

  二核苷磷酸酯的光不稳定（笼）磷酸三酯衍生物的合成和性质

  摘要：

  合成了含有磷酸基团的二核苷磷酸酯，其被邻硝基苄基或邻硝基藜芦酰残基瞬时阻断（笼养）。结果表明，紫外线诱导脱保护的条件在很大程度上取决于保护基团的性质。获得的磷酸三酯对蛇毒磷酸二酯酶和细胞提取物的核酸酶具有抗性。在通过亚磷酰胺方法将修饰的嵌段掺入延伸的寡核苷酸之前，合成含有光不稳定基团的磷酸二核苷。

  DOI：

  10.1007/bf02786343
• 作为产物：
  描述：

  4,4'-双甲氧基三苯甲基氯 在 4-二甲氨基吡啶 作用下， 以 吡啶 为溶剂， 反应 3.0h， 生成 5'-O-(4,4'-dimethoxytrityl)-3'-O-levulinoyl-thymidine
  参考文献：
  名称：

  Design and synthesis of a possible mimic of a thrombin-binding DNA aptamer

  摘要：

  A synthesis is presented of the cyclic trimeric d-oligonucleotide 3'-isopropylphosphate I, comprising one formacetal and two (3' --> 5')-internucleosidic phosphodiester bonds, The ester linkages connect d-guanosine with the 3' and 5' ends of thymidine and 5-hydroxymethyl-2'-deoxyuridine-3'-isopropylphosphate (HMDUpiPr), respectively. The 5'-end of the thymidine unit is anchored via the formacetal bond to the allylic hydroxyl group of HMDUpiPr. The cyclic arrangement of the three d-nucleosides in I mimics, as based on molecular modeling, the key structural features of the conformationally constrained T(7)pG(8)pT(9) p-domain of the thrombin-binding DNA aptamer d(G(1)G(2)T(3)T(4)G(5)G(6)T(7)G(8)T(9)G(10)G(11)T(12)T(13)G(14)G(15)). Biological evaluation showed that compound I did not exhibit anti-thrombin activity. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00351-x

文献信息

• 2,2,5,5-Tetramethylpyrrolidin-3-one-1-sulfinyl Group for 5‘-Hydroxyl Protection of Deoxyribonucleoside Phosphoramidites in the Solid-Phase Preparation of DNA Oligonucleotides
  作者：Vicente Marchán、Jacek Cieślak、Victor Livengood、Serge L. Beaucage

  DOI：10.1021/ja048377i

  日期：2004.8.1

  nitrogen-sulfur reagents have been investigated as potential 5'-hydroxyl protecting groups for deoxyribonucleoside phosphoramidites to improve the synthesis of oligonucleotides on glass microarrays. Out of the nitrogen-sulfur-based protecting groups so far investigated, the 2,2,5,5-tetramethylpyrrolidin-3-one-1-sulfinyl group exhibited near optimal properties for 5'-hydroxyl protection by virtue of the

  已经研究了几种氮硫试剂作为脱氧核糖核苷亚磷酰胺的潜在 5'-羟基保护基团，以改善玻璃微阵列上寡核苷酸的合成。在迄今为止研究的氮硫基保护基团中，2,2,5,5-四甲基吡咯烷-3-one-1-亚磺酰基由于其温和性而表现出近乎最佳的 5'-羟基保护性质。脱保护条件。具体而言，在控制孔玻璃上合成 5'-d(ATCCGTAGCCAAGGTCATGT) 时，末端 5'-亚磺酰胺基团的迭代裂解是通过在酸性盐的存在下用碘处理来有效完成的。寡核苷酸水解为其 2' -脱氧核糖核苷暴露于蛇毒磷酸二酯酶和细菌碱性磷酸酶后未显示任何核碱基加合物或其他修饰的形成。这些发现表明，用于亚磷酰胺 5'-羟基保护的 2,2,5,5-四甲基吡咯烷-3-one-1-亚磺酰基，如 10a-d，可能导致寡核苷酸微阵列的产生，其表现出增强的特异性和检测核酸靶标的灵敏度。
• Oligonucleotide with protected base
  申请人：Ajinomoto Co., Inc.

  公开号：US09371353B2

  公开（公告）日：2016-06-21

  The present invention provides a protected nucleotide for elongation, which can be purified efficiently and in a high yield by a liquid-liquid extraction operation, and can achieve an oligonucleotide production method by a phosphoramidite method. It has been found that the above-mentioned problem can be solved by a particular oligonucleotide comprising a protected base and/or particular oligonucleotide protected by a branched chain-containing aromatic group at 3′-position.

  本发明提供了一种用于延伸的受保护核苷酸，可以通过液液萃取操作高效地和高产率地纯化，并且可以通过磷酰胺酯法实现寡核苷酸的生产方法。已经发现，上述问题可以通过包含受保护碱基和/或在3'-位置含有支链含芳基团的特定寡核苷酸来解决。
• Convergent Solution Phase Synthesis of Chimeric Oligonucleotides by a 2+2 and 3+3 Phosphoramidite Strategy
  作者：Chih-Hau Chen、Wei-Yu Chen、Yu-Chie Chen、Ming-Juan Lee、Chyuan-Der Huang、Kaushik Chanda、Chung-Ming Sun

  DOI：10.1071/ch09298

  日期：——

  A chimeric oligonucleotide tetramer and hexamer were synthesized by the phosphoramidite approach using a 2+2 and 3+3 strategy, respectively. The concept of convergent synthesis provides an efficient route toward the synthesis of longer chimeric oligonucleotides, such as small interfering RNA oligonucleotides without the pollution of n – 1 or shorter failures. This methodology offers an efficient and economical way to scale-up the synthesis of high purity oligonucleotides for clinical trials and commercial uses.

  利用 2+2 和 3+3 策略，通过磷酰胺方法分别合成了嵌合寡核苷酸四聚体和六聚体。聚合合成的概念为合成更长的嵌合寡核苷酸（如小干扰 RNA 寡核苷酸）提供了一条有效的途径，而不会造成 n - 1 或更短的失败。这种方法为临床试验和商业用途的高纯度寡核苷酸的规模化合成提供了一种高效、经济的途径。
• Synthesis of a thymidine dinucleotide analogue containing an internucleotide silyl linkage
  作者：K.K. Ogilvie、J.F. Cormier

  DOI：10.1016/s0040-4039(00)98979-2

  日期：1985.1

  The synthesis of a silyl-linked analogue of a thymidine dinucleotide is described. The use of 5′-dimethoxytrityl and 3′-levulinyl protection allows mild and completely selective deprotection.

  描述了胸苷二核苷酸的甲硅烷基连接的类似物的合成。使用5'-二甲氧基三苯甲基和3'-乙酰丙酰基保护可实现轻度和完全选择性的脱保护。
• Radiologic Agents for Monitoring Alzheimer's Disease Progression and Evaluating a Response to Therapy and Processes for the Preparation of Such Agents
  申请人：Kortylewicz Zbigniew P.

  公开号：US20090117041A1

  公开（公告）日：2009-05-07

  Disclosed are certain cycloSalingenyl pyrimidine nucleoside monophosphates comprising positron emitters or gamma-emitting radiohalides, uses thereof for monitoring Alzheimer's disease progression and evaluating response to therapy and process for their preparation.

  本文披露了包含正电子发射体或伽马辐射放射性卤化物的某些环丝氨基嘧啶核苷酸单磷酸盐，其用于监测阿尔茨海默病的进展并评估对治疗的反应，以及它们的制备过程。