1',2'-dideoxy-β-1'-(3-methylphenyl)-D-ribofuranose | 229469-60-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1',2'-dideoxy-β-1'-(3-methylphenyl)-D-ribofuranose
• 英文别名: (2R,3S,5R)-2-(hydroxymethyl)-5-(3-methylphenyl)oxolan-3-ol
• CAS: 229469-60-7
• 化学式: C₁₂H₁₆O₃
• 分子量: 208.257
• InChiKey: XALFSPXSMVUDLS-QJPTWQEYSA-N

物化性质

• 沸点：
  395.8±42.0 °C(Predicted)
• 密度：
  1.184±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1',2'-dideoxy-β-1'-(3-methylphenyl)-D-ribofuranose 在 4-二甲氨基吡啶 、 频哪酮 、 三乙胺 、 三氟乙酸 作用下， 以 吡啶 、 二氯甲烷 为溶剂， 反应 13.88h， 生成
  参考文献：
  名称：

  扩大胸腺嘧啶等排体生物化学的视野：由胸腺嘧啶和二核苷酸框架中的甲苯残基之间的光反应形成的独特环丁烷二聚体

  摘要：

  取代的甲苯基被认为是胸腺嘧啶残基的紧密等排体。它们可以被 DNA 聚合酶识别，就像它们是胸腺嘧啶一样。由于芳环结构稳定，这些甲苯衍生物通常对自由基加成呈惰性，包括 [2+2] 光环加成，通常用作自由基反应的溶剂。令人惊讶的是，在将甲苯掺入二核苷酸框架后，我们发现紫外线激发的胸腺嘧啶残基很容易通过 [2+2] 光加成反应与甲苯基部分二聚化。此外，甲苯基部分的反应位点不是 C5C6 键，如在环丁烷嘧啶二聚体中常见的那样，而是 C4C5 或 C3C4 键。这种反应模式表明，在堆叠结构中，它是这些键之一，而不是 C5C6，接近胸腺嘧啶 C5C6 键。在 DNA 双链体中发现了类似的结构特征，其中胸腺嘧啶被 2,4-二氟甲苯取代。我们的研究结果表明，虽然取代的甲苯基部分与胸腺嘧啶残基的大小和形状非常相似，但它们的疏水性决定了它们在 DNA 碱基上的堆积与天然胸腺嘧啶残基不同，并可能导致双链

  DOI：

  10.1002/chem.201200816
• 作为产物：
  描述：

  2-deoxy-D-ribose 在 咪唑 、 正丁基锂 、 溴 作用下， 以 四氢呋喃 、 正己烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 150.0h， 生成 1',2'-dideoxy-β-1'-(3-methylphenyl)-D-ribofuranose
  参考文献：
  名称：

  A Set of Nonpolar Thymidine Nucleoside Analogues with Gradually Increasing Size

  摘要：

  [GRAPHICS]We describe a series of nonpolar nucleoside analogues having similar shapes and gradually increasing size. The structure of the nucleobase thymine was mimicked with toluene derivatives, replacing O2/O4 with hydrogen, fluorine, chlorine, bromine, and iodine. Glycosidic bonds were formed by reactions of lithiated 2,4-dihalotoluenes with a deoxyribonolactone derivative. Structural analysis by NMR showed similar conformations across the series. The compounds are useful for study of the biological recognition of nucleotides and nucleic acids.

  DOI：

  10.1021/ol048487u

文献信息

• Optimization of Interstrand Hydrophobic Packing Interactions within Unnatural DNA Base Pairs
  作者：Shigeo Matsuda、Floyd E. Romesberg

  DOI：10.1021/ja047291m

  日期：2004.11.1

  As part of an effort to expand the genetic alphabet, we have evaluated a large number of predominantly hydrophobic unnatural base pairs. We now report the synthesis and stability of unnatural base pairs formed between simple phenyl rings modified at different positions with methyl groups. Surprisingly, several of the unnatural base pairs are virtually as stable as a natural base pair in the same sequence

  作为扩大遗传字母表努力的一部分，我们评估了大量主要为疏水性的非天然碱基对。我们现在报告在不同位置用甲基修饰的简单苯环之间形成的非天然碱基对的合成和稳定性。令人惊讶的是，在同一序列环境中，一些非天然碱基对实际上与天然碱基对一样稳定。结果表明，双链 DNA 内的碱基对稳定性既不需要氢键键合，也不需要大的芳香族表面积，并且可以优化小芳香环之间的链间相互作用以提高稳定性和选择性。这些较小的核碱基预计不会引起双链 DNA 或引物末端的扭曲，这些扭曲似乎限制了较大的非天然碱基对的复制，
• Nonpolar thymidine analogs
  申请人：Kool Todd Eric

  公开号：US20070065360A1

  公开（公告）日：2007-03-22

  Nonpolar thymidine analogs are provided comprising a dihalogenated or trihalogenated base of the structure: where R 1 is a sugar moiety; R 2 is H or CH 3 ; an imaging moiety or a cytotoxic moiety and X 1 and X 2 are independently selected from I, Cl, Br, and F, with the proviso that not more than one F will be present at these positions.

  提供了非极性的胸腺嘧啶类似物，包括结构为的二卤化或三卤化碱基，其中R1是糖基；R2是H或CH3；成像基团或细胞毒基团，以及X1和X2分别选自I、Cl、Br和F，但F在这些位置上不会超过一个。
• Synthesis of <i>C</i>-Aryl-Nucleosides and <i>O</i>-Aryl-Glycosides via Cuprate Glycosylation
  作者：Sven Hainke、Ishwar Singh、Jennifer Hemmings、Oliver Seitz

  DOI：10.1021/jo7016185

  日期：2007.11.1

  useful in many cases, these methods often have drawbacks such as low yields or low economic efficiency. The necessity for intensive optimization of the reaction conditions and/or the use of hazardous and toxic reagents can render C-glycosylation reactions cumbersome. Herein we describe a robust and highly efficient C-glycosylation method. It is shown that aryl cuprates of the Normant-type reliably react

  2'-脱氧Ç在研究DNA-DNA和DNA-蛋白质相互作用，如非天然DNA碱基对-芳基的核苷已经发现越来越重要，并且如基于寡核苷酸的荧光基团。通过几种糖基化方法提供了获得所需的C-芳基-核苷的途径。尽管这些方法在许多情况下有用，但它们通常具有诸如产量低或经济效率低的缺点。强烈优化反应条件和/或使用危险和有毒试剂的必要性会使C-糖基化反应繁琐。在本文中，我们描述了鲁棒且高效的C-糖基化方法。结果表明，诺曼型的芳基铜酸盐可以与霍夫的氯糖可靠地反应，从而释放出C。-芳基-核苷的产率高达93％。该方法可以代替先前采用的与有机镉或-锌物质的偶联。据报道，对于吉尔曼型芳基铜酸盐的C-糖基化有奇特的反应性，这需要对芳烃的具体优化。有趣的是，发现吉尔曼铜酸盐的糖基化不仅提供了对C-芳基-核苷的访问，而且还提供了对O-芳基-糖苷的访问。在氧气存在下，吉尔曼铜酸盐与Hoffer的氯糖1的反应以高达87％的收率提
• Jarchow-Choy, Sarah K.; Sjuvarsson, Elena; Sintim, Herman O., Journal of the American Chemical Society, 2009, vol. 131, p. 5488 - 5494
  作者：Jarchow-Choy, Sarah K.、Sjuvarsson, Elena、Sintim, Herman O.、Eriksson, Staffan、Kool, Eric T.

  DOI：——

  日期：——
• A Series of Nonpolar Thymidine Analogues of Increasing Size:  DNA Base Pairing and Stacking Properties
  作者：Tae Woo Kim、Eric T. Kool

  DOI：10.1021/jo048061t

  日期：2005.3.1

  [GRAPHICS]We describe the properties in DNA of a set of five nonpolar nucleoside mimics in which shape is similar but size is increased gradually. The compounds vary in the size of their exocyclic substituents, which range from hydrogen to iodine, and are designed to test the steric effects of nucleosides, nucleotides, and DNA in biological systems in a systematic way. We describe the conversion of toluene, 2,4-difluorotoluene, 2,4-dichlorotoluene, 2,4-dibromotoluene, and 2,4-diiodotoluene deoxyribosides into suitably protected phosphoramidite derivatives and their incorporation into synthetic DNAs. Studies of their behavior in the context of hexamer and dodecamer duplexes were carried out, with comparison to natural thymine. Thermal melting data with compounds in 5' dangling positions showed that all five compounds stack more strongly than thymine, and all the dihalo-substituted cases stack more strongly than the unsubstituted toluene case. Stacking correlated with surface area and hydrophobicity, both of which increase across the series. In base-pairing studies, all five compounds showed destabilized pairing opposite natural bases (relative to thymine-adenine pairing), as expected. Notably, pairing among the nonpolar base analogues was considerably more stable, and some of the pairs involving the largest analogues showed stability equal to that of a natural thymine-adenine pair. The results establish the base pairing properties of a potentially useful new series of biochemical probes for DNA-protein interactions and also identify a set of new, stable hydrophobic base pairs for designed genetic pairing systems.