9-<5-O-(monomethoxytrityl)-3-deoxy-3-thio-3-S,2-O-diacetyl-β-D-ribofuranosyl>hypoxanthine | 174466-93-4

• 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: 9-<5-O-(monomethoxytrityl)-3-deoxy-3-thio-3-S,2-O-diacetyl-β-D-ribofuranosyl>hypoxanthine
• 英文别名: [(2R,3S,4R,5R)-4-acetylsulfanyl-5-[[(4-methoxyphenyl)-diphenylmethoxy]methyl]-2-(6-oxo-3H-purin-9-yl)oxolan-3-yl] acetate
• CAS: 174466-93-4
• 化学式: C₃₄H₃₂N₄O₇S
• 分子量: 640.717
• InChiKey: PGNQIIQTPCDGBO-JHZZHVAFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.61
• 重原子数：
  46.0
• 可旋转键数：
  10.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  134.63
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  9-<5-O-(monomethoxytrityl)-3-deoxy-3-thio-3-S,2-O-diacetyl-β-D-ribofuranosyl>hypoxanthine 在 吡啶 、 sodium hydroxide 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 8.5h， 生成 Thiophosphoric acid O-[(2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl] ester S-[(2R,3S,4S,5R)-4-hydroxy-2-hydroxymethyl-5-(6-oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-3-yl] ester; compound with triethyl-amine
  参考文献：
  名称：

  Synthesis and Characterization of an RNA Dinucleotide Containing a 3‘-S-Phosphorothiolate Linkage

  摘要：

  The synthesis of an RNA dinucleotide (IspU) containing a 3'-S-phosphorothiolate linkage is described. The compound is prepared from 9-(3-deoxy-3-iodo-beta-D-xylofuranosyl)hyperanthine with installation of the phosphorothiolate group via an Arbusov reaction and protection of the ribose 2'-hydroxyl as a silyl ether. IspU is found to be a substrate for several enzymes including T4 polynucleotide kinase, snake venom phosphodiesterase, and ribonuclease T-2. Base-catalyzed cleavage of the dinucleotide is accelerated (similar to 2000-fold) relative to that of the phosphate-linked compound IpU. Product characterization and kinetic analysis show that IspU is cleaved through the same mechanism as IpU. The observed rate acceleration is argued to reflect stabilization of the anionic transition state by the polarizable sulfur atom.

  DOI：

  10.1021/ja9616903
• 作为产物：
  描述：

  2',3'-anhydroinosine 在 吡啶 、 三氟化硼乙醚 、 sodium iodide 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 49.0h， 生成 9-<5-O-(monomethoxytrityl)-3-deoxy-3-thio-3-S,2-O-diacetyl-β-D-ribofuranosyl>hypoxanthine
  参考文献：
  名称：

  Synthesis and Characterization of an RNA Dinucleotide Containing a 3‘-S-Phosphorothiolate Linkage

  摘要：

  The synthesis of an RNA dinucleotide (IspU) containing a 3'-S-phosphorothiolate linkage is described. The compound is prepared from 9-(3-deoxy-3-iodo-beta-D-xylofuranosyl)hyperanthine with installation of the phosphorothiolate group via an Arbusov reaction and protection of the ribose 2'-hydroxyl as a silyl ether. IspU is found to be a substrate for several enzymes including T4 polynucleotide kinase, snake venom phosphodiesterase, and ribonuclease T-2. Base-catalyzed cleavage of the dinucleotide is accelerated (similar to 2000-fold) relative to that of the phosphate-linked compound IpU. Product characterization and kinetic analysis show that IspU is cleaved through the same mechanism as IpU. The observed rate acceleration is argued to reflect stabilization of the anionic transition state by the polarizable sulfur atom.

  DOI：

  10.1021/ja9616903

文献信息

• Synthesis and structure of S-nucleosidyl S-aryl disulfides and their reaction with phosphites
  作者：Adrian P. Higson、Gerard K. Scott、David J. Earnshaw、Anthony D. Baxter、Roger A. Taylor、Richard Cosstick

  DOI：10.1016/0040-4020(95)00936-1

  日期：1996.1

  corresponding thioesters is described. This procedure has been used for the preparation of a ribonucleoside disulphide (8d), a key intermediate for the synthesis of oligoribonucleotides containing 3′-S-phosphorothiolate linkages. The regioselectivity of the Arbusov reaction of 8d with phosphites has been examined. The X-ray structure of 3′-deoxy-3′-S-(2-nitrophenyldisulfanyl)thymidine (9b) is also reported

  描述了由相应的硫酯制备S-核苷基S-芳基二硫化物的一般方法。该方法已经用于制备核糖核苷二硫化物（8d），核糖核苷二硫化物（8d）是合成含有3'- S-硫代磷酸酯键的寡核糖核苷酸的关键中间体。研究了8d与亚磷酸酯的Arbusov反应的区域选择性。还报道了3′-脱氧-3′- S-（2-硝基苯基二硫烷基）胸苷的X射线结构（9b）。