N⁴-benzoyl-1-[3-C-(hydroxymethyl)-3-deoxy-3-hydroxy-α-L-erythro-tetrafuranosyl] cytosine | 573704-04-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N⁴-benzoyl-1-[3-C-(hydroxymethyl)-3-deoxy-3-hydroxy-α-L-erythro-tetrafuranosyl] cytosine
• 英文别名: N-[1-[(2R,4S)-4-hydroxy-4-(hydroxymethyl)tetrahydrofuran-2-yl]-2-oxo-pyrimidin-4-yl]benzamide；N-[1-[(2R,4S)-4-hydroxy-4-(hydroxymethyl)oxolan-2-yl]-2-oxopyrimidin-4-yl]benzamide
• CAS: 573704-04-8
• 化学式: C₁₆H₁₇N₃O₅
• 分子量: 331.328
• InChiKey: LMFSKTVIDJEZCH-CJNGLKHVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  112
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N⁴-benzoyl-1-[3-C-(hydroxymethyl)-3-deoxy-3-hydroxy-α-L-erythro-tetrafuranosyl] cytosine 在 氨 作用下， 以 甲醇 为溶剂， 生成 1-[3-C-(hydroxymethyl)-3-deoxy-3-hydroxy-α-L-erythro-tetrafuranosyl] cytosine
  参考文献：
  名称：

  Synthesis of novel apionucleosides: a short and concise synthesis of 2-deoxyapio-l-furanosyl acetate from d-lactose

  摘要：

  A series of 2'-deoxyapio-L-furanosyl pyrimidine nucleosides were efficiently synthesized starting from D-lactose via condensation of lactitor acetates with silylated pyrimidine bases under standard Vorbruggen conditions. Their structures were determined by ID and 2D NMR spectroscopy. All the synthesized nucleosides were assayed against several viruses such as HIV-1, HBV, HSV-1, HSV-2, and HCMV. However, none of these compounds had any significant antiviral activity at concentrations up to 100 muM. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(03)00018-1
• 作为产物：
  描述：

  1-O-acetyl-3-C-hydroxymethyl-3,3'-O-isopropylidene-L-glycero-tetrose 在 硫酸氢铵 、 溶剂黄146 、 六甲基二硅氮烷 作用下， 反应 11.0h， 生成 N⁴-benzoyl-1-[3-C-(hydroxymethyl)-3-deoxy-3-hydroxy-α-L-erythro-tetrafuranosyl] cytosine
  参考文献：
  名称：

  Synthesis of novel apionucleosides: a short and concise synthesis of 2-deoxyapio-l-furanosyl acetate from d-lactose

  摘要：

  A series of 2'-deoxyapio-L-furanosyl pyrimidine nucleosides were efficiently synthesized starting from D-lactose via condensation of lactitor acetates with silylated pyrimidine bases under standard Vorbruggen conditions. Their structures were determined by ID and 2D NMR spectroscopy. All the synthesized nucleosides were assayed against several viruses such as HIV-1, HBV, HSV-1, HSV-2, and HCMV. However, none of these compounds had any significant antiviral activity at concentrations up to 100 muM. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(03)00018-1

文献信息

• Synthesis of novel apionucleosides: a short and concise synthesis of 2-deoxyapio-l-furanosyl acetate from d-lactose
  作者：Jihee Kim、Joon Hee Hong

  DOI：10.1016/s0008-6215(03)00018-1

  日期：2003.4

  A series of 2'-deoxyapio-L-furanosyl pyrimidine nucleosides were efficiently synthesized starting from D-lactose via condensation of lactitor acetates with silylated pyrimidine bases under standard Vorbruggen conditions. Their structures were determined by ID and 2D NMR spectroscopy. All the synthesized nucleosides were assayed against several viruses such as HIV-1, HBV, HSV-1, HSV-2, and HCMV. However, none of these compounds had any significant antiviral activity at concentrations up to 100 muM. (C) 2003 Elsevier Science Ltd. All rights reserved.