methyl-3-deoxy-3-azido-5-O-para-monomethoxytrityl-2-mesyloxy-α-D-arabinofuranose | 153206-10-1

• 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: methyl-3-deoxy-3-azido-5-O-para-monomethoxytrityl-2-mesyloxy-α-D-arabinofuranose
• 英文别名: [(2S,3S,4R,5S)-4-azido-2-methoxy-5-[[(4-methoxyphenyl)-diphenylmethoxy]methyl]oxolan-3-yl] methanesulfonate
• CAS: 153206-10-1
• 化学式: C₂₇H₂₉N₃O₇S
• 分子量: 539.609
• InChiKey: JRRCLAMBONYRKE-XPGKHFPBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  38
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  103
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  methyl-3-deoxy-3-azido-5-O-para-monomethoxytrityl-2-mesyloxy-α-D-arabinofuranose 在 lithium aluminium tetrahydride 、 叔丁基二甲硅基三氟甲磺酸酯 作用下， 以 乙醚 、 乙腈 为溶剂， 反应 12.0h， 生成 1-(5-O-para-monomethoxytrityl-2,3-dideoxy-epimino-β-D-ribofuranosyl)thymine
  参考文献：
  名称：

  Synthesis of Some New Nucleoside Analogues as Potential Antiviral Agents

  摘要：

  A novel series of pyrimidine nucleoside analogues was synthesized. 2,3-Dideoxy-2,3-anhydro-beta-D-lyxofuranose was opened by sodium azide to give the corresponding azido compound, which was reduced by lithium aluminium hydride to lead to 2,3-dideoxy-2,3-epimino-beta-D-ribofuranose. Pyrimidine bases were glycosylated with this synthon to give potential antiviral molecules : 1-(2,3-dideoxy-2,3-epimino-beta-D-ribofuranosyl)pyrimidines.

  DOI：

  10.1080/07328319308018562
• 作为产物：
  描述：

  methyl 2,3-anhydro-α-D-lyxofuranoside 在 吡啶 、 sodium azide 、 ammonium chloride 作用下， 以 乙醇 、 水 为溶剂， 反应 106.0h， 生成 methyl-3-deoxy-3-azido-5-O-para-monomethoxytrityl-2-mesyloxy-α-D-arabinofuranose
  参考文献：
  名称：

  Synthesis of Some New Nucleoside Analogues as Potential Antiviral Agents

  摘要：

  A novel series of pyrimidine nucleoside analogues was synthesized. 2,3-Dideoxy-2,3-anhydro-beta-D-lyxofuranose was opened by sodium azide to give the corresponding azido compound, which was reduced by lithium aluminium hydride to lead to 2,3-dideoxy-2,3-epimino-beta-D-ribofuranose. Pyrimidine bases were glycosylated with this synthon to give potential antiviral molecules : 1-(2,3-dideoxy-2,3-epimino-beta-D-ribofuranosyl)pyrimidines.

  DOI：

  10.1080/07328319308018562

文献信息

• Synthesis of Some New Nucleoside Analogues as Potential Antiviral Agents
  作者：M. A. Forestier、A. I. Ayi、R. Condom、B. P. Boyode、J. N. Colin、J. Selway、R. Challand、R. Guedj

  DOI：10.1080/07328319308018562

  日期：1993.11

  A novel series of pyrimidine nucleoside analogues was synthesized. 2,3-Dideoxy-2,3-anhydro-beta-D-lyxofuranose was opened by sodium azide to give the corresponding azido compound, which was reduced by lithium aluminium hydride to lead to 2,3-dideoxy-2,3-epimino-beta-D-ribofuranose. Pyrimidine bases were glycosylated with this synthon to give potential antiviral molecules : 1-(2,3-dideoxy-2,3-epimino-beta-D-ribofuranosyl)pyrimidines.