[(2R,3R,5R)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] selenocyanate | 220792-24-5

• 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: [(2R,3R,5R)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] selenocyanate
• CAS: 220792-24-5
• 化学式: C₁₇H₂₇N₃O₄SeSi
• 分子量: 444.465
• InChiKey: HVOFEIGNPCTCBZ-MGPQQGTHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.13
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  91.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [(2R,3R,5R)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] selenocyanate 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以24%的产率得到bis(5'-O-tert-butyldimethylsilyl-3'-deoxythymidine)-3'-β,3'-β-diselenide
  参考文献：
  名称：

  NEW 3′-DEOXYTHYMIDINES BEARING A NUCLEOPHILIC 3′-SUBSTITUENT

  摘要：

  New potential cancer-driven as well as HIV-driven nucleoside heteroanalogs, such as 3'-thio- and 3'- as well as 5'-selenosubstituted thymidines, have been synthesized. We also report an effective method for the preparation of novel nucleoside derivatives, bis(deoxynucleoside) diselenides, in nearly quantitative yields. The North conformation is significantly populated in the conformational equilibrium for-3'-alpha -alkylthiothymidines.

  DOI：

  10.1081/ncn-100001439
• 作为产物：
  描述：

  5’-O-(叔丁基二甲基甲硅烷基)胸苷 在 吡啶 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 24.0h， 生成 [(2R,3R,5R)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] selenocyanate
  参考文献：
  名称：

  New nucleoside heteroanalogues: Desoxynucleoside selenocyanates

  摘要：

  Naw nucleoside heteroanalogues, 5'- and 9'-desoxynucleoside selenocyanates and primary desoxysugar selenocyanates, were synthesized from activated nucleoside and sugar derivatives and a new convenient seleno nucleophile, tetrabutylammonium selenocyanate. Tresylate-based activation of hydroxy functions turned out to be most successful for formation of these selenocyanates compared with mesylate- or triflate-based activation. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)02559-3