5'-<(tert-butyldiphenyl)silyl>-2',3'-dideoxycytidine | 143840-02-2

• 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: 5'-<(tert-butyldiphenyl)silyl>-2',3'-dideoxycytidine
• 英文别名: 4-amino-1-[(2R,5S)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]oxolan-2-yl]pyrimidin-2-one
• CAS: 143840-02-2
• 化学式: C₂₅H₃₁N₃O₃Si
• 分子量: 449.625
• InChiKey: KOTSFFBBGPFTAA-WMZHIEFXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.08
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  77.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5'-<(tert-butyldiphenyl)silyl>-2',3'-dideoxycytidine 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 66.0h， 生成 5'-<(tert-butyldiphenyl)silyl>-N⁴-(1,8-dioxooctyl-Trp-Val-Sta-CH(Ph)-CH2Ph)-2',3'-dideoxycytidine
  参考文献：
  名称：

  Peptide-Nucleoside Conjugates: Synthesis and Anti-HIV Activities

  摘要：

  New peptide-nucleosides which consist of an anti-RT nucleoside and anti-protease peptide moieties, were designed in order to investigate their anti-HIV-1 properties. The synthesis of these new analogues was achieved using BOP coupling reagent which avoided the protection and deprotection steps of the 5'-OH group of the nucleoside part. These new compounds tested on MT(4) infected cells show no increase in anti-HIV activities compared to that of the component pieces. Interestingly we found that the 5'-(tert-butyldiphenyl)silyl analogues show anti-HIV activities equivalent to that of the 5'-free OH corresponding compounds. This result suggests a possible interaction of these compounds at a non-substrate binding site of the reverse transcriptase.

  DOI：

  10.1080/15257779508010699
• 作为产物：
  描述：

  叔丁基二苯基氯硅烷 、 2,3-二脱氧胞啶 以 吡啶 为溶剂， 以72%的产率得到5'-<(tert-butyldiphenyl)silyl>-2',3'-dideoxycytidine
  参考文献：
  名称：

  Peptide-Nucleoside Conjugates: Synthesis and Anti-HIV Activities

  摘要：

  New peptide-nucleosides which consist of an anti-RT nucleoside and anti-protease peptide moieties, were designed in order to investigate their anti-HIV-1 properties. The synthesis of these new analogues was achieved using BOP coupling reagent which avoided the protection and deprotection steps of the 5'-OH group of the nucleoside part. These new compounds tested on MT(4) infected cells show no increase in anti-HIV activities compared to that of the component pieces. Interestingly we found that the 5'-(tert-butyldiphenyl)silyl analogues show anti-HIV activities equivalent to that of the 5'-free OH corresponding compounds. This result suggests a possible interaction of these compounds at a non-substrate binding site of the reverse transcriptase.

  DOI：

  10.1080/15257779508010699

文献信息

• CHU, CHUNG K.;BEACH, WARREN J. WARREN;BABU, J. RAMESH;JEONG, LAK SHIN;JEO+, NUCLEOSIDES AND NUCLEOTIDES, 10,(1991) N-3, C. 423-426
  作者：CHU, CHUNG K.、BEACH, WARREN J. WARREN、BABU, J. RAMESH、JEONG, LAK SHIN、JEO+

  DOI：——

  日期：——