3'-O-(1,3-benzodithiol-2-yl)thymidine | 84752-64-7

• 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: 3'-O-(1,3-benzodithiol-2-yl)thymidine
• 英文别名: 1-[(2R,4S,5R)-4-(1,3-benzodithiol-2-yloxy)-5-(hydroxymethyl)tetrahydrofuran-2-yl]-5-methyl-pyrimidine-2,4-dione；1-[(2R,4S,5R)-4-(1,3-benzodithiol-2-yloxy)-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 84752-64-7
• 化学式: C₁₇H₁₈N₂O₅S₂
• 分子量: 394.472
• InChiKey: NURYBASUACHHMD-MISXGVKJSA-N

物化性质

• 密度：
  1.54±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  139
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3'-O-(1,3-benzodithiol-2-yl)thymidine 在 偶氮二异丁腈 、 三正丁基氢锡 、 mercury dichloride 作用下， 以 水 、 乙腈 为溶剂， 反应 4.0h， 生成 beta-胸苷
  参考文献：
  名称：

  [[2-(Methylthio)phenyl]thio]methyl (MTPM): a new protecting group of hydroxyl groups capable of conversion to a methyl group

  摘要：

  DOI：

  10.1021/jo00286a041
• 作为产物：
  描述：

  3'-O-(1,3-benzodithiol-2-yl)-5'-O-isobutyloxycarbonylthymidine 在 氨 作用下， 以 甲醇 为溶剂， 反应 8.0h， 以95%的产率得到3'-O-(1,3-benzodithiol-2-yl)thymidine
  参考文献：
  名称：

  Cyclic orthoester functions as new protecting groups in nucleosides

  摘要：

  DOI：

  10.1021/ja00345a062

文献信息

• Synthesis of Benzodithiol-2-yl-Substituted Nucleoside Derivatives as Lead Compounds Having Anti-Bovine Viral Diarrhea Virus Activity
  作者：Kohji Seio、Takahide Sasaki、Koichirou Yanagida、Masanori Baba、Mitsuo Sekine

  DOI：10.1021/jm049677d

  日期：2004.10.1

  Nucleoside derivatives having a benzodithiol-2-yl (BDT) group were synthesized and examined for their anti-bovine viral diarrhea virus (BVDV) activities. Other substituents structurally similar to the BDT group such as 1,3-benzodioxol-2-yl, benzimidazol-2-yl and 1-oxo-benzodithiol-2-yl groups were not effective as the pharmacophore. The anti-BVDV assay revealed that 2'-O-BDT-guanosine and 2'-O-BDT-inosine

  合成具有苯并二硫醇-2-基（BDT）基团的核苷衍生物，并检查其抗牛病毒性腹泻病毒（BVDV）的活性。结构上与BDT基团相似的其他取代基，例如1，3-苯并二恶唑-2-基，苯并咪唑-2-基和1-氧-苯并二硫醇-2-基均不能用作药效基团。抗BVDV分析表明，在本研究合成的核苷衍生物中，2'-O-BDT-鸟苷和2'-O-BDT-肌苷具有最强的抗BVDV活性。由于BVDV已被公认是人类丙型肝炎病毒（HCV）的替代物，因此BDT修饰的核苷可能成为寻找核苷型抗HCV药物（如病毒唑）的一类新型先导化合物。
• Acylphosphonates
  作者：Mitsuo Fujii、Kouji Ozaki、Mitsuo Sekine、Tsujiaki Hata

  DOI：10.1016/s0040-4020(01)81630-6

  日期：1987.1

  synthesized by a new method via dideoxyribonucleoside 2,2,2-trichloroethoxycarbonylphosphonates and aroylphosphonates. The conversion of dideoxyribonucleoside 2,2,2-trichloroethoxycarbonylphosphonates to dideoxyribonucleoside trimethylsilyl phosphites by treatment with Me3SiCl-Zn-acetylacetone proceeded with retention configuration at phosphorus. The silyl phosphite intermediates were converted to the phosphorothioates

  通过二脱氧核糖核苷2,2,2-三氯乙氧基羰基膦酸酯和芳酰基膦酸酯通过新方法合成了脱氧核糖核苷硫代磷酸酯。通过用Me 3 SiCl-Zn-乙酰丙酮处理，将双脱氧核糖核苷2,2,2-三氯乙氧基羰基膦酸酯转化为双脱氧核糖核苷三甲基甲硅烷基亚磷酸酯，在磷处具有保留构型。通过用硫原位处理将亚磷酸甲硅烷基酯中间体转化为硫代磷酸酯。通过n-BuNH 2的作用，很容易将芳酰基从8-11上除去，并通过单质硫处理原位转化为双脱氧核糖核苷硫代磷酸酯中的仅一种非对映异构体（Rp-构型）。
• Acylphosphonates. 5. 1A new method for stereospecific generation of phosphorothioate via aroylphosphonate intermediate
  作者：Mitsuo Fujii、Kouji Ozaki、Akiko Kume、Mitsuo Sekine、TsujiaKi Hata

  DOI：10.1016/s0040-4039(00)84142-8

  日期：1986.1

  Dideoxynucleoside phosphorothioates were synthesized by a new method via dideoxynucleoside aroylphosphonates. The aroyl groups were easily removed from and 2 by the action of n-BuNH2 and in situ converted to only one diastereomer (Rp-configuration) of dideoxynucleoside phosphorothioates by treatment with elemental sulfur.

  脱氧核苷硫代磷酸酯是通过双脱氧核苷芳酰基膦酸酯通过新方法合成的。通过n-BuNH 2的作用，很容易从α2和α2中除去芳基，并通过用元素硫处理原位转化为双脱氧核苷硫代磷酸酯的仅一种非对映异构体（Rp-构型）。
• The case for configurational stability of H-phosphonate diesters in the presence of diazabicyclo[5.4.0]undec-7-ene (DBU)
  作者：T Johansson

  DOI：10.1016/s0968-0896(01)00140-7

  日期：2001.9

  Configurational stability of dinucleoside H-phosphonates and the stereochemical course of their sulfurisation in the presence of diazabicyclo[5.4.0]undec-7-ene (DBU) were investigated using P-31 NMR spectroscopy. It was found that under the reaction conditions and irrespective of the type of protecting groups present in the nucleoside moieties, the H-phosphonate diesters investigated did not undergo any detectable epimerisation at the phosphorus centre, and their sulfurisation with elemental sulfur in the presence of DBU, proceeded stereo specifically. Thus, we could not confirm reports from another laboratory on a stereoselective course of sulfurisation of H-phosphonate diesters and the corresponding acylphosphonates in the presence of DBU. (C) 2001 Elsevier Science Ltd. All rights reserved.
• 4,4',4''-Tris(benzoyloxy)trityl as a new type of base-labile group for protection of primary hydroxyl groups
  作者：Mitsuo Sekine、Tsujiaki Hata

  DOI：10.1021/jo00166a014

  日期：1983.9