1-[(2R,3S)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-3-hydroxy-2,3-dihydro-furan-2-yl]-1H-pyrimidine-2,4-dione | 135824-36-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 1-[(2R,3S)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-3-hydroxy-2,3-dihydro-furan-2-yl]-1H-pyrimidine-2,4-dione
• 英文别名: 1-[(2R,3S)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-3-hydroxy-2,3-dihydrofuran-2-yl]pyrimidine-2,4-dione
• CAS: 135824-36-1
• 化学式: C₁₅H₂₄N₂O₅Si
• 分子量: 340.451
• InChiKey: ZHMDNSOABXSMOH-WCQYABFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.33
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  93.55
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 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 、 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 3.17h， 生成 1-[(2R,3S)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-3-hydroxy-2,3-dihydro-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

• Stereoselective synthesis of 4′-C-branched 2,′3′-didehydro-2′-dideoxy nucleosides based on SnCl4-promoted allylic rearrangement
  作者：Kazuhiro Haraguchi、Hiromichi Tanaka、Yoshiharu Itoh、Shigeru Saito、Tadashi Miyasaka

  DOI：10.1016/s0040-4039(00)78874-5

  日期：1992.5

  Based on SnCl4-promoted allylic rearrangement between a 3',4'-unsaturated uracil nucleoside and organosilicon reagents, stereoselective introduction of carbon functionalities to the 4'-position has been accomplished, disclosing a new entry for a series of 4'-C-branched nucleosides of biological interests.