1-[(2R,3R,4S,5R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-4-hydroxy-3-phenylselanyl-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione | 135824-32-7

• 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: 1-[(2R,3R,4S,5R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-4-hydroxy-3-phenylselanyl-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione
• 英文别名: 1-[(2R,3R,4S,5R)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-4-hydroxy-3-phenylselanyloxolan-2-yl]pyrimidine-2,4-dione
• CAS: 135824-32-7
• 化学式: C₂₁H₃₀N₂O₅SeSi
• 分子量: 497.525
• InChiKey: DJTNRCKHCQECPM-QXCFHYIPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.63
• 重原子数：
  30.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  93.55
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  1-[(2R,3R,4S,5R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-4-hydroxy-3-phenylselanyl-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione 在 三乙胺 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 5.5h， 生成 1-[(R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-4-oxo-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  Selenoxide elimination for the synthesis of unsaturated-sugar uracil nucleosides

  摘要：

  Introduction of a phenylseleno group to the sugar portion of uracil nucleosides and selenoxide elimination reactions of the resulting selenium-containing derivatives are described. A phenylselenide anion prepared by reducing (PhSe)2 with LialH4 was found to be highly reactive. By using this selenide as a nucleophile, ring openings of various types of cyclonucleosides and nucleosides having an anhydro structure in the sugar portion were accomplished. The products, which contain a phenylseleno group in the sugar portion, were oxidized with m-CPBA in CH2Cl2, and their susceptibility to the selenoxide elimination and regiochemistry of the reaction was investigated.

  DOI：

  10.1021/jo00018a038
• 作为产物：
  描述：

  5’-O-三苯甲基尿苷-2’,3’-来苏-环氧化物 在 吡啶 、 sodium tetrahydroborate 、 溶剂黄146 作用下， 反应 0.17h， 生成 1-[(2R,3R,4S,5R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-4-hydroxy-3-phenylselanyl-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  Selenoxide elimination for the synthesis of unsaturated-sugar uracil nucleosides

  摘要：

  Introduction of a phenylseleno group to the sugar portion of uracil nucleosides and selenoxide elimination reactions of the resulting selenium-containing derivatives are described. A phenylselenide anion prepared by reducing (PhSe)2 with LialH4 was found to be highly reactive. By using this selenide as a nucleophile, ring openings of various types of cyclonucleosides and nucleosides having an anhydro structure in the sugar portion were accomplished. The products, which contain a phenylseleno group in the sugar portion, were oxidized with m-CPBA in CH2Cl2, and their susceptibility to the selenoxide elimination and regiochemistry of the reaction was investigated.

  DOI：

  10.1021/jo00018a038

文献信息

• 2',3'-Cyclopropanated Nucleoside Dimers
  作者：Constantin Yannopoulos、Wen-Qiang Zhou、Peter Nower、Didier Peoc'h、Yogesh Sanghvi、George Just

  DOI：10.1055/s-1997-802

  日期：1997.4

  Syntheses of three novel conformationally rigid dimers containing cyclopropyl -amide and -sulfonamide functionalities are described. Their incorporation into an oligonucleotide sequence resulted in considerable lowering of the Tm's in binding to their complementary RNA sequences.

  本文描述了三种新型构象刚性二聚体的合成，这些二聚体含有环丙基酰胺和磺酰胺功能基团。将其引入寡核苷酸序列后，在与其互补RNA序列结合时，Tm值显著降低。