[(2R,3R,4S,5R)-4-Hydroxy-5-hydroxymethyl-2-(4-hydroxy-2-oxo-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-acetonitrile | 185142-00-1

• 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: [(2R,3R,4S,5R)-4-Hydroxy-5-hydroxymethyl-2-(4-hydroxy-2-oxo-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-acetonitrile
• 英文别名: 2-[(2R,3R,4S,5R)-2-(2,4-dioxopyrimidin-1-yl)-4-hydroxy-5-(hydroxymethyl)oxolan-3-yl]acetonitrile
• CAS: 185142-00-1
• 化学式: C₁₁H₁₃N₃O₅
• 分子量: 267.241
• InChiKey: SAJQSLRFTZESIP-GTDKDYCYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  123
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [(2R,3R,4S,5R)-4-Hydroxy-5-hydroxymethyl-2-(4-hydroxy-2-oxo-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-acetonitrile 在 吡啶 、 二异丙基铵盐四氮唑 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 20.0h， 生成 2'-deoxy-2'-α-C-2'-(cyanomethyl)-5'-O-(4,4'-dimethoxytrityl)uridine-[(2-cyanoethyl)-N,N-diisopropyl]phosphoramidite
  参考文献：
  名称：

  含2'- C-酰氨基烷基和2'- C-氰基烷基的寡脱氧核糖核苷酸的合成及其对互补DNA和RNA的杂交亲和力评估

  摘要：

  合成了含有2'- C-支链核苷且酰胺或腈附接到一个或两个碳烷基链上的寡脱氧核苷酸。制备2'- C-修饰的核苷的亚磷酰胺，并使用自动DNA合成将其掺入寡核苷酸中。通过紫外熔解实验测量了具有互补RNA和DNA的双链体稳定性，以评估酰胺/腈功能是否可以在不存在2'-氧的情况下诱导任何双链体稳定性。在没有2'-氧的情况下，含有2'- C-修饰的寡核苷酸的双链体稳定性降低。

  DOI：

  10.1016/j.tet.2006.11.024
• 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 吡啶 、 4-二甲氨基吡啶 、 ammonium hydroxide 、 sodium chlorite 、 sodium periodate 、 potassium dihydrogenphosphate 、 N-羟基丁二酰亚胺 、 四氧化锇 、 2-甲基-2-丁烯 、 N-甲基吗啉氧化物 、 triethylamine tris(hydrogen fluoride) 、 N,N'-二环己基碳二亚胺 、 三氟乙酸酐 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 、 丙酮 、 叔丁醇 为溶剂， 反应 18.84h， 生成 [(2R,3R,4S,5R)-4-Hydroxy-5-hydroxymethyl-2-(4-hydroxy-2-oxo-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-acetonitrile
  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

文献信息

• 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.
• Syntheses of 2′-C-amidoalkyl and 2′-C-cyanoalkyl containing oligodeoxyribonucleotides and assessment of their hybridisation affinity for complementary DNA and RNA
  作者：Lavinia Brennan、Richard Cosstick、Ian A. O'Neil、Arthur Van Aerschot

  DOI：10.1016/j.tet.2006.11.024

  日期：2007.1

  Oligodeoxynucleotides containing 2′-C-branched nucleosides with an amide or nitrile appended to either a one or two carbon alkyl chain have been synthesised. The phosphoramidites of the 2′-C-modified nucleosides were prepared and incorporated into the oligonucleotides using automated DNA synthesis. The duplex stability with complementary RNA and DNA was measured by UV melting experiments, in order

  合成了含有2'- C-支链核苷且酰胺或腈附接到一个或两个碳烷基链上的寡脱氧核苷酸。制备2'- C-修饰的核苷的亚磷酰胺，并使用自动DNA合成将其掺入寡核苷酸中。通过紫外熔解实验测量了具有互补RNA和DNA的双链体稳定性，以评估酰胺/腈功能是否可以在不存在2'-氧的情况下诱导任何双链体稳定性。在没有2'-氧的情况下，含有2'- C-修饰的寡核苷酸的双链体稳定性降低。