1-<2,5-dideoxy-5-(phenylseleno)-β-D-threo-pentofuranosyl>thymine | 117901-57-2

• 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-<2,5-dideoxy-5-(phenylseleno)-β-D-threo-pentofuranosyl>thymine
• 英文别名: 1-(2,5-Dideoxy-5-phenylselenenyl-β-D-threo-pentofuranosyl)thymine；1-[2,5-dideoxy-5-(phenylseleno)-β-D-threo-pentofuranosyl]thymine；1-[(2R,4R,5S)-4-hydroxy-5-(phenylselanylmethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 117901-57-2
• 化学式: C₁₆H₁₈N₂O₄Se
• 分子量: 381.29
• InChiKey: IEHONGWDMRDXRN-MGPQQGTHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.06
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  78.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-<2,5-dideoxy-5-(phenylseleno)-β-D-threo-pentofuranosyl>thymine 在 咪唑 、 三乙胺 、 间氯过氧苯甲酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 1-[3-O-(tert-butyldimethylsilyl)-2,5-dideoxy-β-L-glycero-pent-4-enofuranosyl]thymine
  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：

  1-((2R,4R,5S)-5-(iodomethyl)-4-((4-methoxytetrahydro-2H-pyran-4-yl)oxy)tetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione 在 silver(I) acetate 、 溶剂黄146 作用下， 以 异丙醇 、 乙腈 为溶剂， 反应 3.0h， 生成 1-<2,5-dideoxy-5-(phenylseleno)-β-D-threo-pentofuranosyl>thymine
  参考文献：
  名称：

  Action of nucleophiles on 2,3′-anhydrothymidine: side-reactions involving the possible intermediacy of 2,5′-anhydro-1-(2-deoxy---Threo-pentofuranosyl) thymine

  摘要：

  2,3'-Anhydrothymidine (1) reacts with the sodium salt of propane-2-thiol and with sodium phenyl selenide to give 5'-substituted products [(3b) and (3c), respectively] in addition to the expected 3'-substituted 2',3'-dideoxynucleoside derivatives [(2b) and (2c)].

  DOI：

  10.1016/s0040-4039(00)74215-8

文献信息

• Preparation of γ- and δ-Phenylselenenyl Alcohols via Ring Cleavage of Oxetane and Oxolane
  作者：Kazuhiro Haraguchi、Hiromichi Tanaka、Tadashi Miyasaka

  DOI：10.1055/s-1989-27275

  日期：——

  Various types of oxetanes and oxolanes can be cleaved by reaction with phenylselenide anion prepared from diphenyl diselenide and lithium aluminum hydride in dioxane.

  在二噁烷中与二苯基二硒化物和氢化铝锂制备的苯基硒化物阴离子反应，可以裂解各种类型的氧杂环丁烷和氧杂环戊烷。
• Cleavage of Cyclic Ethers Including Oxetane and Oxolane with a Highly Nucleophilic Species of Phenylselenide Anion
  作者：Kazuhiro Haraguchi、Hiromichi Tanaka、Hiroyuki Hayakawa、Tadashi Miyasaka

  DOI：10.1246/cl.1988.931

  日期：1988.6.5

  Phenylselenide anion generated from (PhSe)2 and LiAlH4, was found to be highly reactive to various types of cyclic ethers, providing a new method to prepare γ- and δ-phenylselenenyl alcohols from oxetane and oxolane, respectively.

  发现由 (PhSe)2 和 LiAlH4 生成的苯硒阴离子对各种类型的环醚具有高度反应性，为分别从氧杂环丁烷和氧杂环戊烷制备 γ- 和 δ- 苯基硒醇提供了一种新方法。