2'-deoxy-2'-α-C-(acetoxymethyl)uridine | 692781-24-1

• 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: 2'-deoxy-2'-α-C-(acetoxymethyl)uridine
• 英文别名: [(2R,3R,4S,5R)-2-(2,4-dioxopyrimidin-1-yl)-4-hydroxy-5-(hydroxymethyl)oxolan-3-yl]methyl acetate
• CAS: 692781-24-1
• 化学式: C₁₂H₁₆N₂O₇
• 分子量: 300.268
• InChiKey: SOBLZGPJIVYBTF-DEKFOEGESA-N

物化性质

• 密度：
  1.454±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.03
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  130.85
• 氢给体数：
  3.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  2'-deoxy-2'-α-C-(acetoxymethyl)uridine 在 二异丙基铵盐四氮唑 作用下， 以 吡啶 、 二氯甲烷 为溶剂， 生成 [(2R,3R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-[2-cyanoethoxy-[di(propan-2-yl)amino]phosphanyl]oxy-2-(2,4-dioxopyrimidin-1-yl)oxolan-3-yl]methyl acetate
  参考文献：
  名称：

  The synthesis of 2′-homouridine, its incorporation into a dinucleoside monophosphate and hydrolytic behaviour of the dimer

  摘要：

  An efficient route to 2'-homouridine (1), a new nucleoside analogue, is reported that is based on an ene reaction. This nucleoside has been incorporated into a dinucleoside monophosphate and hydrolytic studies on the dimer show that it does not behave like a ribonucleotide. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01478-6
• 作为产物：
  描述：

  1-((2R,3R,3aS,9aR)-3-Allyl-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-2-yl)-4-hydroxy-1H-pyrimidin-2-one 在 sodium tetrahydroborate 、 臭氧 、 triethylamine tris(hydrogen fluoride) 作用下， 以 四氢呋喃 、 吡啶 、 二氯甲烷 为溶剂， 反应 16.26h， 生成 2'-deoxy-2'-α-C-(acetoxymethyl)uridine
  参考文献：
  名称：

  The synthesis of 2′-homouridine, its incorporation into a dinucleoside monophosphate and hydrolytic behaviour of the dimer

  摘要：

  An efficient route to 2'-homouridine (1), a new nucleoside analogue, is reported that is based on an ene reaction. This nucleoside has been incorporated into a dinucleoside monophosphate and hydrolytic studies on the dimer show that it does not behave like a ribonucleotide. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01478-6

文献信息

• Synthesis and transcription studies on 5′-triphosphates derived from 2′-C-branched-uridines: 2′-homouridine-5′-triphosphate is a substrate for T7 RNA polymerase
  作者：John B. J. Pavey、Anthony J. Lawrence、Ian A. O'Neil、Stefan Vortler、Richard Cosstick

  DOI：10.1039/b314348a

  日期：——

  The 5'-triphosphates of 2'-hydroxymethyluridine (2'-homouridine) and 2'-hydroxyethyluridine were prepared from the corresponding acetyl-protected nucleosides by initial phosphitylation with 2-chloro-5,6-benzo-1,2,3-dioxaphosphorin-4-one. 2'-Acetamidouridine 5'-triphosphate was prepared in an analogous fashion from uridine 2'-C-, 3'-O-gamma-butyrolactone, in which the 3'-hydroxyl group is internally

  2'-羟基甲基尿苷（2'-高尿嘧啶）和2'-羟基乙基尿苷的5'-三磷酸酯是由相应的乙酰基保护的核苷通过用2-氯-5,6-苯并-1,2,3-进行的磷酸化作用而制备的。二氧磷磷-4-一。由尿苷2′-C-，3′-O-γ-丁内酯以类似的方式制备2′-乙酰胺基尿苷5′-三磷酸酯，其中3′-羟基在内部被保护为内酯。随后用氨处理得到所需的三磷酸乙酰氨基酯。研究了所有三种三磷酸酯作为T7 RNA聚合酶的底物和该酶的Y639F突变体。2' 发现在甲基锰的存在下，三磷酸合尿苷是野生型酶的底物，并且被特异地掺入到短RNA转录物中（长度为20和21个核苷酸）。通过其对碱水解的抗性证实了转录物中存在类似物。凝胶电泳分析还表明，可以将2'-同型尿苷与长度为75个核苷酸的转录物多重结合。这是2'-脱氧2'-α-C分支的5'-三磷酸核苷充当T7 RNA聚合酶底物的首次报道。2'-羟乙基-和2'-乙酰氨基-尿苷三磷酸不是酶
• 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.
• The synthesis of a novel 2′,3′-cyclic phosphate derived from 2′-homouridine
  作者：John B.J. Pavey、Richard Cosstick、Ian A. O'Neil

  DOI：10.1016/s0040-4039(98)01952-2

  日期：1998.11

  The novel 2',3'-cyclic phosphate (1) derived from 2'-homouridine has been prepared by phosphorylation with 2-cyanocthyl N,N,N',N' -tetrapropylphosphorodiamidite. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.