1-(3-cyano-3-deoxy-5-O-trityl-β-D-arabinofuranosyl)thymine | 115941-56-5

• 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: 1-(3-cyano-3-deoxy-5-O-trityl-β-D-arabinofuranosyl)thymine
• 英文别名: (2S,3S,4S,5R)-4-hydroxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)-2-(trityloxymethyl)oxolane-3-carbonitrile
• CAS: 115941-56-5
• 化学式: C₃₀H₂₇N₃O₅
• 分子量: 509.561
• InChiKey: YKHKQAKVZBYQCI-WTVRZORLSA-N

物化性质

• 密度：
  1.36±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  38
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  112
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-(3-cyano-3-deoxy-5-O-trityl-β-D-arabinofuranosyl)thymine 在 三乙基硅烷 、 Wilkinson's catalyst 、 N,N'-硫羰基二咪唑 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 48.0h， 生成 1-(3'-cyano-2',3'-dideoxy-5'-O-trityl-β-D-threo-pentofuranosyl)thymine
  参考文献：
  名称：

  Synthesis and Anti-HIV Activity of 3'-Cyano-2',3'-dideoxythymidine and 3'-Cyano-2',3'-didehydro-2',3'-dideoxythymidine

  摘要：

  DOI：

  10.3987/com-88-4708
• 作为产物：
  描述：

  1-(2,3-epoxy-5-O-trityl-β-D-lyxo-pentofuranosyl)thymine 生成 1-(3-cyano-3-deoxy-5-O-trityl-β-D-arabinofuranosyl)thymine
  参考文献：
  名称：

  HERDEWIJN, PIET;BALZARINI, JAN;BADA, MASANORI;PAUWELS, RUDI;VAN, AERSCHOT+, J. MED. CHEM., 31,(1988) N 10, C. 2040-2048

  摘要：

  DOI：

文献信息

• Synthesis and anti-HIV activity of different sugar-modified pyrimidine and purine nucleosides
  作者：Piet Herdewijn、Jan Balzarini、Masanori Baba、Rudi Pauwels、Arthur Van Aerschot、Gerard Janssen、Erik De Clercq

  DOI：10.1021/jm00118a033

  日期：1988.10

  A series of base-modified pyrimidine 3'-azido-2',3'-dideoxynucleosides and 3'-substituted purine and pyrimidine 2',3'-dideoxynucleosides have been synthesized and evaluated for their inhibitory activity against human immunodeficiency virus (HIV) replication in MT-4 cells. The following pyrimidine derivatives emerged as the most potent and/or selective inhibitors of HIV-induced cytopathogenicity (in order of decreasing selectivity: 3'-azido-3'-deoxythymidine (AZT), 3'-azido-2',3'-dideoxyuridine (AzddUrd), 3'-azido-2',3'-dideoxy-5-methylcytidine (AzddMeCyd), 3'-fluoro-ddUrd (FddUrd), 3'-fluoro-ddThd (FddThd), the N4-hydroxylated derivative of AzddMeCyd and the N4-methylated derivative of AzddMeCyd. Among the purine 2',3'-dideoxynucleosides, 3'-azido-2',3'-dideoxyguanosine (AzddGuo), 3'-fluoro-ddGuo (FddGuo), and 3'-fluoro-2,6-diaminopurine 2',3'-dideoxynucleoside (FddDAPR) were the most selective inhibitors of HIV replication.
• Synthesis and Anti-HIV Activity of 3'-Cyano-2',3'-dideoxythymidine and 3'-Cyano-2',3'-didehydro-2',3'-dideoxythymidine
  作者：Akira Matsuda、Mutsumi Satoh、Hideki Nakashima、Naoki Yamamoto、Tohru Ueda

  DOI：10.3987/com-88-4708

  日期：——
• HERDEWIJN, PIET;BALZARINI, JAN;BADA, MASANORI;PAUWELS, RUDI;VAN, AERSCHOT+, J. MED. CHEM., 31,(1988) N 10, C. 2040-2048
  作者：HERDEWIJN, PIET、BALZARINI, JAN、BADA, MASANORI、PAUWELS, RUDI、VAN, AERSCHOT+

  DOI：——

  日期：——