1-((2R,3R,4S,5R)-3-{2-[1-(2-Fluoro-phenyl)-4-methoxy-piperidin-4-yloxy]-ethyl}-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-dione | 171503-91-6

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 1-((2R,3R,4S,5R)-3-{2-[1-(2-Fluoro-phenyl)-4-methoxy-piperidin-4-yloxy]-ethyl}-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-dione
• 英文别名: 1-[(2R,3R,4S,5R)-3-[2-[1-(2-fluorophenyl)-4-methoxypiperidin-4-yl]oxyethyl]-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
• CAS: 171503-91-6
• 化学式: C₂₃H₃₀FN₃O₇
• 分子量: 479.506
• InChiKey: MXXRSZXXQSWYBR-DPDLHNOKSA-N

物化性质

• 密度：
  1.41±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.59
• 重原子数：
  34.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  126.25
• 氢给体数：
  3.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  1-((2R,3R,4S,5R)-3-{2-[1-(2-Fluoro-phenyl)-4-methoxy-piperidin-4-yloxy]-ethyl}-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-dione 在 吡啶 、 二异丙基铵盐四氮唑 作用下， 以 二氯甲烷 为溶剂， 反应 17.0h， 生成 3-[[(2R,3S,4R,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(2,4-dioxopyrimidin-1-yl)-4-[2-[1-(2-fluorophenyl)-4-methoxypiperidin-4-yl]oxyethyl]oxolan-3-yl]oxy-[di(propan-2-yl)amino]phosphanyl]oxypropanenitrile
  参考文献：
  名称：

  Synthesis and Properties of 2‘-Deoxy-2‘-α-C-branched Nucleosides and Nucleotides

  摘要：

  Four functionalized 2'-deoxy-2'-alpha-C-branched nucleosides, namely, 2'-deoxy-2'-alpha-C-(carboxymethyl)-uridine, 2'-deoxy-2'-alpha-acetamidouridine, 2'-deoxy-2'-alpha-C-(hydroxyethyl)uridine, and 2'-deoxy-2'-alpha-C-(2,3-dihydroxypropyl)uridine, have been prepared. Conversion of these nucleosides to their appropriately protected phosphoramidites, followed by tetrazole-induced reaction with 2',3'-di-O-acetyluridine, oxidation, and subsequent deprotection furnished the corresponding dinucleoside monophosphates. During the oxidation of the amide-derived phosphite, partial dehydration occurred to give a mixture of the amide- and nitrile-containing dimers. Interestingly, the ratio of amide to nitrile could be largely controlled by choice of oxidant. The hydroxyethyl- and dihydroxypropyl-modified dimers were particularly resistant to snake venom phosphodiesterase-catalyzed hydrolysis (relative half-lives of 129 and 120, respectively, in comparison to UpU). It is anticipated that these nucleoside analogues will ultimately be used in the construction of ribozymes containing enhanced functionality and nuclease resistance.

  DOI：

  10.1021/jo9614607
• 作为产物：
  描述：

  1-((2R,3R,3aS,9aR)-3-{2-[1-(2-Fluoro-phenyl)-4-methoxy-piperidin-4-yloxy]-ethyl}-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-2-yl)-1H-pyrimidine-2,4-dione 在 triethylamine tris(hydrogen fluoride) 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 生成 1-((2R,3R,4S,5R)-3-{2-[1-(2-Fluoro-phenyl)-4-methoxy-piperidin-4-yloxy]-ethyl}-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  功能化的2'- C-支链核苷通过其γ-丁内酯的日光浴

  摘要：

  已经制备了包含羧酸（2），伯酰胺（3）或伯羟基（4）的官能化的2'- C-支链核苷，并研究了它们对寡核苷酸合成的保护。还显示了2'- C- 3'- O - γ-丁内酯（5）是制备这些类似物的有用中间体。

  DOI：

  10.1016/0040-4039(95)01226-8

文献信息

• The Synthesis of 2′-C-Functionalised Nucleosides for Incorporation into Catalytic RNA
  作者：Anthony J. Lawrence、John B. J. Pavey、Ian A. O'Neil、Richard Cosstick

  DOI：10.1080/07328319708006215

  日期：1997.7

  Five 2'-C-functionalized nucleosides (1-5) have been prepared and incorporated into dinucleoside monophosphates. The effect of the functionality on the stability of the adjacent phosphodiester bond toward hydrolysis by nuclease enzymes and extremes of pH has been assessed.