3'-β-(phenylselenyl)-5'-O-trityl-3'-deoxythymidine | 131933-46-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 3'-β-(phenylselenyl)-5'-O-trityl-3'-deoxythymidine
• 英文别名: 5-methyl-1-[(2R,4R,5R)-4-phenylselanyl-5-(trityloxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
• CAS: 131933-46-5
• 化学式: C₃₅H₃₂N₂O₄Se
• 分子量: 623.61
• InChiKey: NZISGNVTOLTFRN-XWHIBYANSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.96
• 重原子数：
  42
• 可旋转键数：
  9
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  67.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3'-β-(phenylselenyl)-5'-O-trityl-3'-deoxythymidine 在 双氧水 、 溶剂黄146 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.25h， 生成 司他夫定
  参考文献：
  名称：

  Selenium nucleophiles for the preparation of antiviral nucleosides

  摘要：

  The reactivity of nucleophilic selenium species toward nucleoside derivatives has been examined. A number of new 2'-deoxyribose nucleosides have been synthesized using this methodology. The cis elimination of the selenoxide obtained from the oxidation of the corresponding phenylselenide has been shown to be an efficient method for the preparation of the 2',3'-unsaturated antiviral nucleoside 1-(2,3-dideoxy-beta-D-glycero-pent-2-enofuranosyl)thymine (DAT).

  DOI：

  10.1021/jo00006a037
• 作为产物：
  描述：

  1-(2-deoxy-3-O-methanesulfonyl-5-O-trityl-β-D-ribopentofuranosyl)thymine 、 二苯基二硒醚 在 lithium aluminium tetrahydride 作用下， 生成 3'-β-(phenylselenyl)-5'-O-trityl-3'-deoxythymidine
  参考文献：
  名称：

  Selenium nucleophiles for the preparation of antiviral nucleosides

  摘要：

  The reactivity of nucleophilic selenium species toward nucleoside derivatives has been examined. A number of new 2'-deoxyribose nucleosides have been synthesized using this methodology. The cis elimination of the selenoxide obtained from the oxidation of the corresponding phenylselenide has been shown to be an efficient method for the preparation of the 2',3'-unsaturated antiviral nucleoside 1-(2,3-dideoxy-beta-D-glycero-pent-2-enofuranosyl)thymine (DAT).

  DOI：

  10.1021/jo00006a037

文献信息

• COSFORD, NICHOLAS D. P.;SCHINAZI, RAYMOND F., J. ORG. CHEM., 56,(1991) N, C. 2161-2165
  作者：COSFORD, NICHOLAS D. P.、SCHINAZI, RAYMOND F.

  DOI：——

  日期：——