1-<3-O-benzyl-2,4-bis-O-<(2,4-dichlorophenoxy)(thiocarbonyl)>-6-O-trityl-β-D-allopyranosyl>thymine | 149067-53-8

• 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-O-benzyl-2,4-bis-O-<(2,4-dichlorophenoxy)(thiocarbonyl)>-6-O-trityl-β-D-allopyranosyl>thymine
• 英文别名: 1-{3-O-benzyl-2,4-bis-O-[(2,4-dichlorophenoxy)(thiocarbonyl)]-6-O-trityl-β-D-allopyranosyl}thymine；1-[(2R,3R,4R,5R,6R)-3,5-bis[(2,4-dichlorophenoxy)carbothioyloxy]-4-phenylmethoxy-6-(trityloxymethyl)oxan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 149067-53-8
• 化学式: C₅₁H₄₀Cl₄N₂O₉S₂
• 分子量: 1030.83
• InChiKey: VAECTJODBUCLPH-NXNGGWSOSA-N

物化性质

• 密度：
  1.50±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  12.9
• 重原子数：
  68
• 可旋转键数：
  18
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  178
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  1-<3-O-benzyl-2,4-bis-O-<(2,4-dichlorophenoxy)(thiocarbonyl)>-6-O-trityl-β-D-allopyranosyl>thymine 在 palladium dihydroxide 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 乙醇 、 环己烯 、 苯 为溶剂， 反应 95.67h， 生成 1-(2,4-dideoxy-β-D-erythro-hexopyranosyl)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：

  O,O-二(三甲基甲硅烷基)胸苷 在 吡啶 、 4-二甲氨基吡啶 、 氨 、 四氯化锡 作用下， 以 甲醇 、 1,2-二氯乙烷 为溶剂， 反应 117.83h， 生成 1-<3-O-benzyl-2,4-bis-O-<(2,4-dichlorophenoxy)(thiocarbonyl)>-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