[(2R,3R,4R,5R)-4-acetyloxy-2-[[[(2R,3S,4R,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-(cyanomethyl)-5-(2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxy-(2-cyanoethoxy)phosphoryl]oxymethyl]-5-(2,4-dioxopyrimidin-1-yl)oxolan-3-yl] acetate | 199480-62-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: [(2R,3R,4R,5R)-4-acetyloxy-2-[[[(2R,3S,4R,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-(cyanomethyl)-5-(2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxy-(2-cyanoethoxy)phosphoryl]oxymethyl]-5-(2,4-dioxopyrimidin-1-yl)oxolan-3-yl] acetate
• CAS: 199480-62-1
• 化学式: C₄₈H₄₉N₆O₁₇P
• 分子量: 1012.92
• InChiKey: POBPVBOTKZVKQF-ZQKQEXQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  72
• 可旋转键数：
  23
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  290
• 氢给体数：
  2
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  [(2R,3R,4R,5R)-4-acetyloxy-2-[[[(2R,3S,4R,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-(cyanomethyl)-5-(2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxy-(2-cyanoethoxy)phosphoryl]oxymethyl]-5-(2,4-dioxopyrimidin-1-yl)oxolan-3-yl] acetate 在 甲醇 、 氨 、 溶剂黄146 作用下， 反应 2.0h， 生成 Phosphoric acid (2R,3S,4R,5R)-4-cyanomethyl-2-hydroxymethyl-5-(4-hydroxy-2-oxo-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester (2R,3S,4R,5R)-3,4-dihydroxy-5-(4-hydroxy-2-oxo-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester
  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：

  [(2R,3R,3aS,9aR)-2-(4-Hydroxy-2-oxo-2H-pyrimidin-1-yl)-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-3-yl]-acetaldehyde 在 吡啶 、 2,6-二甲基吡啶 、 四氮唑 、 4-二甲氨基吡啶 、 ammonium hydroxide 、 sodium chlorite 、 potassium dihydrogenphosphate 、 N-羟基丁二酰亚胺 、 2-甲基-2-丁烯 、 二异丙基铵盐四氮唑 、 碘 、 triethylamine tris(hydrogen fluoride) 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 水 、 乙腈 、 叔丁醇 为溶剂， 反应 35.0h， 生成 [(2R,3R,4R,5R)-4-acetyloxy-2-[[[(2R,3S,4R,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-(cyanomethyl)-5-(2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxy-(2-cyanoethoxy)phosphoryl]oxymethyl]-5-(2,4-dioxopyrimidin-1-yl)oxolan-3-yl] acetate
  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

• 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.