[(2R,3R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-2-(4-hydroxy-2-oxo-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-acetic acid benzhydryl ester | 185141-90-6

• 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,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-2-(4-hydroxy-2-oxo-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-acetic acid benzhydryl ester
• 英文别名: benzhydryl 2-[(2R,3R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-2-(2,4-dioxopyrimidin-1-yl)-4-hydroxyoxolan-3-yl]acetate
• CAS: 185141-90-6
• 化学式: C₄₅H₄₂N₂O₉
• 分子量: 754.836
• InChiKey: OYQWXJWCCBPFTE-FAQXXKCISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  56
• 可旋转键数：
  15
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  133
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  [(2R,3R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-2-(4-hydroxy-2-oxo-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-acetic acid benzhydryl ester 在 2,6-二甲基吡啶 、 四氮唑 、 二异丙基铵盐四氮唑 、 碘 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 乙腈 为溶剂， 反应 16.83h， 生成 benzhydryl 2-[(2R,3R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-[2-cyanoethoxy-[[(2R,3R,4R,5R)-3,4-diacetyloxy-5-(2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy]phosphoryl]oxy-2-(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
• 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 吡啶 、 triethylamine tris(hydrogen fluoride) 作用下， 以 四氢呋喃 、 二氯甲烷 、 丙酮 为溶剂， 反应 4.5h， 生成 [(2R,3R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-2-(4-hydroxy-2-oxo-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-acetic acid benzhydryl ester
  参考文献：
  名称：

  The Synthesis of 2′-C-Functionalised Nucleosides for Incorporation into Catalytic RNA

  摘要：

  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.

  DOI：

  10.1080/07328319708006215

文献信息

• Synthesis and duplex stability of oligodeoxyribonucleotides containing a 2′→5′-amide linkage
  作者：Mai-Yee Chan、Robin A. Fairhurst、Stephen P. Collingwood、Julie Fisher、John R. P. Arnold、Richard Cosstick、Ian A. O’Neil

  DOI：10.1039/a808505f

  日期：——

  2′-Deoxy-2′-α-C-carboxymethyl-3′-O-tert-butyldimethylsilyl-5′-O-dimethoxytrityluridine (11a) and the corresponding 3′-deoxy derivative 2′,3′-dideoxy-2′-α-C-carboxymethyl-5′-O-dimethoxytrityluridine (11b) have been condensed with 5′-amino-5′-deoxythymidine to prepare dinucleotide analogues (5a and 5b) which contain a 2′→5′-amide linkage. These dimer units have been incorporated into deoxynucleotide dodecamers using solid-phase phosphoramidite chemistry. Thermal melting studies show that a single 2′→5′-amide linkage in a deoxyoligonucleotide has a considerable destabilising effect on duplexes formed with both the DNA and RNA complementary sequences. Interestingly, the amide linkage has a significantly greater destabilising influence in the DNA duplexes than in the RNA hybrids.

  2-脱氧-2-脱氧-C-羧甲基-3-O-叔丁基二甲基甲硅烷基-5-O-二甲氧基三苯甲基尿苷(11a)和相应的3-脱氧衍生物2-， 3-二脱氧-2-α-C-羧甲基-5-O-二甲氧基三苯甲基尿苷 (11b) 与 5-氨基-5-脱氧胸苷缩合以制备二核苷酸类似物（5a 和 5b） ），其中包含2-5-酰胺键。使用固相亚磷酰胺化学将这些二聚体单元整合到脱氧核苷酸十二聚体中。热熔解研究表明，脱氧寡核苷酸中的单个 2-5-酰胺键对由 DNA 和 RNA 互补序列形成的双链体具有相当大的不稳定作用。有趣的是，酰胺键在 DNA 双链体中比在 RNA 杂合体中具有显着更大的不稳定影响。
• 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.
• 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.