1-(2′,3′,5′-tri-O-benzoyl-β-D-ribofuranosyl)-4-pyrimidone | 52523-26-9

• 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: 1-(2′,3′,5′-tri-O-benzoyl-β-D-ribofuranosyl)-4-pyrimidone
• 英文别名: 2',3',5'-tri-O-benzoyl-1-(β-D-ribofuranosyl)-4-pyrimidinone；2',3',5'-tri-O-benzoyl-β-D-ribosyl-4(1H)pyrimidinone；1-(tri-O-benzoyl-β-D-ribofuranosyl)-1H-pyrimidin-4-one；1-(2,3,5-Tri-O-benzoyl-β-D-ribofuranosyl)-1,4-dihydropyrimidin-4-on；1-(2,3,5-Tri-O-benzoyl-beta-D-ribofuranosyl)-1,4-dihydropyrimidine-4-one；[(2R,3R,4R,5R)-3,4-dibenzoyloxy-5-(4-oxopyrimidin-1-yl)oxolan-2-yl]methyl benzoate
• CAS: 52523-26-9
• 化学式: C₃₀H₂₄N₂O₈
• 分子量: 540.529
• InChiKey: JJFMFVWTLFISTP-MIRJVGOZSA-N

物化性质

• 沸点：
  689.6±65.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  40
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  121
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1-(2′,3′,5′-tri-O-benzoyl-β-D-ribofuranosyl)-4-pyrimidone 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以92%的产率得到4-pyrimidinone 1-β-D-riboside
  参考文献：
  名称：

  Desulfurization of 2-thiouracil nucleosides: Conformational studies of 4-pyrimidinone nucleosides

  摘要：

  4-Pyrimidinone ribofuranoside (H(2)o(4)U) and 4-pyrimidinone 2 '-deoxyribofuranoside (dH(2)o(4)U) were synthesized by the oxidative desulfurization of parent 2-thiouracil nucleosides with m-chloroperbenzoic acid. The crystal structures of H(2)o(4)U and dH(2)o(4)U and their conformations in solution were determined and compared with corresponding 2-thiouracil and uracil nucleosides. The absence of a large 2-thiocarbonyl/2-carbonyl group in the nucleobase moiety results in C2'-endo puckering of the ribofuranose ring (S conformer) in the crystal structure of H(2)o(4)U, which is not typical of RNA nucleosides. Interestingly, the hydrogen bonding network in the crystals of dH(2)o(4)U stabilizes the sugar moiety conformation in the C3'-endo form (N conformer), rarely found in DNA nucleosides. In aqueous solution, dH(2)o(4)U reveals a similar population of the C2'-endo conformation (65%) to that of 2'-deoxy-2-thiouridine (62%), while the 62% population of the S conformer for H(2)o(4)U is significantly different from that of the parent 2-thiouridine, for which the N conformer is dominant (71%). Such a difference may be of biological importance, as the desulfurization process of natural tRNA 2-thiouridines may occur under conditions of oxidative stress in the cell and may influence the decoding process. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.02.008
• 作为产物：
  描述：

  2’,3’,5’-三-O-苯甲酰基-2-硫代尿苷 在 2-(Phenylsulfonyl)-3-phenyloxaziridin 作用下， 以 二氯甲烷 为溶剂， 生成 1-(2′,3′,5′-tri-O-benzoyl-β-D-ribofuranosyl)-4-pyrimidone
  参考文献：
  名称：

  使用反式-2-（苯磺酰基）-3-苯基恶唑烷将2-硫代嘧啶核苷有效脱硫为相应的4-嘧啶酮类似物

  摘要：

  用反式-2-苯基磺酰基-3-苯基恶唑烷酮（PSO）对2-硫代嘧啶核苷（s 2 U ∗）进行简短处理，可以有效地进行底物脱硫，从而生成相应的4-嘧啶酮酮类似物（H 2 U ∗）。关键的转化过程是通过将2-硫代羰基氧化为硫代含氧酸衍生物，然后消除二氧化硫而进行的。4-嘧啶酮1-β-d-核糖苷（H 2U）已转化为相应的亚磷酰胺，这是一种随时可用的单体，用于将修饰的核苷引入寡核苷酸链。而且，如MALDI-TOF质谱法所证实的，通过用PSO处理TdA（s 2 U）dGdC寡核苷酸，可以直接在寡核苷酸水平上实现2-硫尿苷核苷酸的有效脱硫。

  DOI：

  10.1016/j.tetlet.2004.07.052

文献信息

• Transformations of thiopyrimidine and thiopurine nucleosides following oxidation with dimethyldioxirane
  作者：Raffaele Saladino、Enrico Mincione、Claudia Crestini、Maurizio Mezzetti

  DOI：10.1016/0040-4020(96)00289-x

  日期：1996.5

  and convenient method for the synthesis of several pyrimidine and purine nucleosides by selective oxidation of thionucleosides with dimethyldioxirane is reported. Thioketo moieties in the C-4 position of the pyrimidine ring, and in the C-6, and C-8 positions of the purine ring are the domain of oxidative nucleophilic substitution. Thioketo moieties in the C-2 position of both purine and pyrimidine rings

  报道了通过用二甲基二环氧乙烷选择性氧化硫代核苷来合成几种嘧啶和嘌呤核苷的通用且方便的方法。嘧啶环的C-4位，嘌呤环的C-6和C-8位的Thioketo部分是氧化亲核取代的结构域。嘌呤和嘧啶环的C-2位的Thioketo部分是脱硫或二硫化物形成的区域。
• Efficient desulfurization of 2-thiopyrimidine nucleosides to the corresponding 4-pyrimidinone analogues using trans-2-(phenylsulfonyl)-3-phenyloxaziridine
  作者：Elżbieta Sochacka、Iwona Frątczak

  DOI：10.1016/j.tetlet.2004.07.052

  日期：2004.8

  A brief treatment of 2-thiopyrimidine nucleosides (s2U∗) with trans-2-phenylsulfonyl-3-phenyloxaziridine (PSO) results in efficient substrate desulfurization leading to the corresponding 4-pyrimidinone analogues (H2U∗). The key transformation proceeds through oxidation of the 2-thiocarbonyl group to a sulfur oxyacid derivative and subsequent elimination of sulfur dioxide. 4-Pyrimidinone 1-β-d-riboside

  用反式-2-苯基磺酰基-3-苯基恶唑烷酮（PSO）对2-硫代嘧啶核苷（s 2 U ∗）进行简短处理，可以有效地进行底物脱硫，从而生成相应的4-嘧啶酮酮类似物（H 2 U ∗）。关键的转化过程是通过将2-硫代羰基氧化为硫代含氧酸衍生物，然后消除二氧化硫而进行的。4-嘧啶酮1-β-d-核糖苷（H 2U）已转化为相应的亚磷酰胺，这是一种随时可用的单体，用于将修饰的核苷引入寡核苷酸链。而且，如MALDI-TOF质谱法所证实的，通过用PSO处理TdA（s 2 U）dGdC寡核苷酸，可以直接在寡核苷酸水平上实现2-硫尿苷核苷酸的有效脱硫。
• Improved synthesis of oligonucleotides containing 2-thiouridine derivatives by use of diluted iodine solution
  作者：Itaru Okamoto、Kohji Seio、Mitsuo Sekine

  DOI：10.1016/j.tetlet.2005.11.044

  日期：2006.1

  2-thiocarbonyl group of 2-thiouridine (s2U) derivatives reacts easily with various oxidizing agents used in oligonucleotide synthesis to give a complex mixture. In this letter, we report an improved method for the synthesis of oligonucleotides containing s2U derivatives. It turned out that the 2-thiocarbonyl group of oligonucleotides containing s2U derivatives was stable in a 0.02 M solution of iodine

  已知2-硫尿苷（s 2 U）衍生物的2-硫羰基容易与寡核苷酸合成中使用的各种氧化剂反应而得到复杂的混合物。在这封信中，我们报告了一种用于合成含有s 2 U衍生物的寡核苷酸的改进方法。结果表明，含s 2 U衍生物的寡核苷酸的2-硫羰基在0.02 M碘的吡啶-THF-H 2 O溶液中是稳定的。这些条件成功地用于合成含s 2的寡核苷酸自动DNA / RNA合成仪上的U衍生物。此外，未检测到不良的副反应，因此可以显着提高产率获得这些修饰的寡核苷酸。
• Nucleoside analogs
  申请人：Ribozyme Pharmaceuticals, Inc.

  公开号：US06248878B1

  公开（公告）日：2001-06-19

  Novel nucleoside analogs, such as 3-(&bgr;-D-Ribofuranosyl)-2-fluoropyridine, 3-(&bgr;-D-Ribofuranosyl)-pyridin-2-one, 3-(&bgr;-D-Ribofuranosyl)-pyridin-2-(4-nitrophenylethyl)-one, 3-(&agr;-D-Ribofuranosyl)-2-fluoropyridine, 5-(&bgr;-D-Ribofuranosyl)-2-bromopyridine, 5-(&agr;-D-Ribofuranosyl)-2-bromopyridine, 5-(&bgr;-D-Ribofuranosyl)-pyridin-2-one, 5-(&agr;-D-Ribofuranosyl)-pyridin-2-one, 5-(&bgr;-D-Ribofuranosyl)-2-aminopyridine, 5-(&bgr;-D-Ribofuranosyl)-pyridin-2-(4-nitrophenylethyl)-one, and 5-(&agr;-D-Ribofuranosyl)-2-aminopyridine; process for their synthesis and incorporation into polynucleotides.

  新型核苷类似物，例如3-（&bgr;-D-核糖呋喃基）-2-氟吡啶，3-（&bgr;-D-核糖呋喃基）-吡啶-2-酮，3-（&bgr;-D-核糖呋喃基）-吡啶-2-（4-硝基苯乙基）-酮，3-（&agr;-D-核糖呋喃基）-2-氟吡啶，5-（&bgr;-D-核糖呋喃基）-2-溴吡啶，5-（&agr;-D-核糖呋喃基）-2-溴吡啶，5-（&bgr;-D-核糖呋喃基）-吡啶-2-酮，5-（&agr;-D-核糖呋喃基）-吡啶-2-酮，5-（&bgr;-D-核糖呋喃基）-2-氨基吡啶，5-（&bgr;-D-核糖呋喃基）-吡啶-2-（4-硝基苯乙基）-酮和5-（&agr;-D-核糖呋喃基）-2-氨基吡啶；它们的合成过程以及它们被纳入多核苷酸的过程。
• Process for the production of 2'-branched nucleosides
  申请人：Idenix (Cayman) Limited

  公开号：EP2319853A1

  公开（公告）日：2011-05-11

  The present invention provides an improved process for preparing β-D and β-L 2'-C-methyl-nucleosides and 2'-C-methyl-3'-O-ester nucleosides

  本发明提供了一种制备 β-D 和 β-L 2'-C- 甲基核苷和 2'-C- 甲基-3'-O-酯核苷的改进工艺