1-(2,4,6-tri-O-benzoyl-3-O-benzyl-β-D-allopyranosyl)thymine | 149067-50-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(2,4,6-tri-O-benzoyl-3-O-benzyl-β-D-allopyranosyl)thymine
• 英文别名: Bz(-2)[Bn(-3)][Bz(-4)][Bz(-6)]All(b)-thymin-1-yl；[(2R,3R,4R,5R,6R)-3,5-dibenzoyloxy-6-(5-methyl-2,4-dioxopyrimidin-1-yl)-4-phenylmethoxyoxan-2-yl]methyl benzoate
• CAS: 149067-50-5
• 化学式: C₃₉H₃₄N₂O₁₀
• 分子量: 690.706
• InChiKey: AWQUAJCZRKJKIK-MRKLFBNESA-N

物化性质

• 密度：
  1.38±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  51
• 可旋转键数：
  14
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  147
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  1-(2,4,6-tri-O-benzoyl-3-O-benzyl-β-D-allopyranosyl)thymine 在 吡啶 、 氨 作用下， 以 甲醇 为溶剂， 反应 112.0h， 生成 1-(3-O-benzyl-6-O-trityl-β-D-allopyranosyl)thymine
  参考文献：
  名称：

  Synthesis of 2,4-dideoxy-.beta.-D-erythro-hexopyranosyl nucleosides

  摘要：

  The synthesis of 1-(2,4-dideoxy-beta-D-erythro-hexopyranosyl)thymine (12)1 was accomplished using two different synthetic routes. It was obtained starting either from 1,2:5,6-di-O-isopropylidene-alpha-D-glucofuranose or from tri-O-acetyl-D-glucal. The other modified nucleosides, with either a cytosine, guanine, or adenine moiety, were synthesized using the second reaction scheme. Deoxygenation reactions were accomplished with the (2,4-dichlorophenoxy)thiocarbonyl derivatives generated in situ.

  DOI：

  10.1021/jo00063a013
• 作为产物：
  描述：

  二丙酮-D-葡萄糖 在 吡啶 、 ammonium hydroxide 、 四氯化锡 、 sodium hydride 、 溶剂黄146 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 37.0h， 生成 1-(2,4,6-tri-O-benzoyl-3-O-benzyl-β-D-allopyranosyl)thymine
  参考文献：
  名称：

  Synthesis of 2,4-dideoxy-.beta.-D-erythro-hexopyranosyl nucleosides

  摘要：

  The synthesis of 1-(2,4-dideoxy-beta-D-erythro-hexopyranosyl)thymine (12)1 was accomplished using two different synthetic routes. It was obtained starting either from 1,2:5,6-di-O-isopropylidene-alpha-D-glucofuranose or from tri-O-acetyl-D-glucal. The other modified nucleosides, with either a cytosine, guanine, or adenine moiety, were synthesized using the second reaction scheme. Deoxygenation reactions were accomplished with the (2,4-dichlorophenoxy)thiocarbonyl derivatives generated in situ.

  DOI：

  10.1021/jo00063a013

文献信息

• Synthesis of 2,4-dideoxy-.beta.-D-erythro-hexopyranosyl nucleosides
  作者：Koen Augustyns、Jef Rozenski、Arthur Van Aerschot、Gerard Janssen、Piet Herdewijn

  DOI：10.1021/jo00063a013

  日期：1993.5

  The synthesis of 1-(2,4-dideoxy-beta-D-erythro-hexopyranosyl)thymine (12)1 was accomplished using two different synthetic routes. It was obtained starting either from 1,2:5,6-di-O-isopropylidene-alpha-D-glucofuranose or from tri-O-acetyl-D-glucal. The other modified nucleosides, with either a cytosine, guanine, or adenine moiety, were synthesized using the second reaction scheme. Deoxygenation reactions were accomplished with the (2,4-dichlorophenoxy)thiocarbonyl derivatives generated in situ.