Uridine 2'-deoxy-2'-α-C,3'-O-γ-butyrolactone | 171503-84-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃类
• 英文名称: Uridine 2'-deoxy-2'-α-C,3'-O-γ-butyrolactone
• 英文别名: 1-[(3aR,4R,6R,6aS)-6-(hydroxymethyl)-2-oxo-3a,4,6,6a-tetrahydro-3H-furo[2,3-c]furan-4-yl]pyrimidine-2,4-dione
• CAS: 171503-84-7
• 化学式: C₁₁H₁₂N₂O₆
• 分子量: 268.226
• InChiKey: QHMZHZGNTDLGPF-FNIZFGCXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  105
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Uridine 2'-deoxy-2'-α-C,3'-O-γ-butyrolactone 在 吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.5h， 生成 5'-O-(tert-Butyldimethylsilyl)-2'-deoxy-2'-α-C-[N-(5'-deoxythymidin-5'-yl)carbamoylmethyl]uridine
  参考文献：
  名称：

  Lawrence, Anthony J.; Pavey, John B. J.; Chan, Mai-Yee, Journal of the Chemical Society. Perkin transactions I, 1997, # 18, p. 2761 - 2767

  摘要：

  DOI：
• 作为产物：
  描述：

  2'-deoxy-2'-α-C-carboxymethyl-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)uridine 在 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 19.0h， 生成 Uridine 2'-deoxy-2'-α-C,3'-O-γ-butyrolactone
  参考文献：
  名称：

  Lawrence, Anthony J.; Pavey, John B. J.; Chan, Mai-Yee, Journal of the Chemical Society. Perkin transactions I, 1997, # 18, p. 2761 - 2767

  摘要：

  DOI：

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
• Sunthesis of functionalised 2′-C-branched nucleosides via their γ-butyrolactones
  作者：Anthony J. Lawrence、John B.J. Pavey、Ian A. O'Neil、Richard Cosstick

  DOI：10.1016/0040-4039(95)01226-8

  日期：1995.8

  Functionalised 2′-C-branched nucleosides that contain either a carboxylic acid (2), a primary amide (3) or a primary hydroxyl (4) group have been prepared and their protection for oligonucleotide synthesis investigated. The 2′-C-3′-O-γ-butyrolactone (5) was also shown to be a useful intermediate for the preparation of these analogues.

  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。
• Synthesis and Properties of 2‘-Deoxy-2‘-α-<i>C</i>-branched Nucleosides and Nucleotides
  作者：Anthony J. Lawrence、John B. J. Pavey、Richard Cosstick、Ian A. O'Neil

  DOI：10.1021/jo9614607

  日期：1996.1.1

  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.
• Lawrence, Anthony J.; Pavey, John B. J.; Chan, Mai-Yee, Journal of the Chemical Society. Perkin transactions I, 1997, # 18, p. 2761 - 2767
  作者：Lawrence, Anthony J.、Pavey, John B. J.、Chan, Mai-Yee、Fairhurst, Robin A.、Collingwood, Stephen P.、Fisher, Julie、Cosstick, Richard、O'Neil, Ian A.

  DOI：——

  日期：——