10-[[(4S,5S,6R)-6-[[(3aR,4S,6R,6aR)-6-(hydroxymethyl)-2-(4-methoxyphenyl)-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]oxymethyl]-5-hydroxy-2-(4-methoxyphenyl)-1,3-dioxan-4-yl]methyl]-7,8-dimethylbenzo[g]pteridine-2,4-dione | 136738-78-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 10-[[(4S,5S,6R)-6-[[(3aR,4S,6R,6aR)-6-(hydroxymethyl)-2-(4-methoxyphenyl)-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]oxymethyl]-5-hydroxy-2-(4-methoxyphenyl)-1,3-dioxan-4-yl]methyl]-7,8-dimethylbenzo[g]pteridine-2,4-dione
• CAS: 136738-78-8
• 化学式: C₃₈H₄₀N₄O₁₂
• 分子量: 744.755
• InChiKey: KZHHTSGCFAXXMX-DGRNHIMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.28
• 重原子数：
  54.0
• 可旋转键数：
  10.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  194.94
• 氢给体数：
  3.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  10-[[(4S,5S,6R)-6-[[(3aR,4S,6R,6aR)-6-(hydroxymethyl)-2-(4-methoxyphenyl)-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]oxymethyl]-5-hydroxy-2-(4-methoxyphenyl)-1,3-dioxan-4-yl]methyl]-7,8-dimethylbenzo[g]pteridine-2,4-dione 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以52 mg的产率得到lampteroflavin
  参考文献：
  名称：

  Chemical synthesis of lampteroflavin as light emitter in the luminous mushroom, lampteromyces japonicus

  摘要：

  The synthesis of lampteroflavin (the light emitter of the luminous mushroom, Lampteromyces japonicus) is described. Protected riboflavin was stereoselectively glycosylated with ribofuranosyl imidate to give largely the alpha-product. Chloroethyl group which could be removed under neutral condition contributed to this synthesis.

  DOI：

  10.1016/s0040-4020(01)86553-4
• 作为产物：
  描述：

  2',4'-O-p-Methoxybenzylidene 5'-O-trityl-riboflavin 在 三氟化硼乙醚 、 四丁基氟化铵 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 10-[[(4S,5S,6R)-6-[[(3aR,4S,6R,6aR)-6-(hydroxymethyl)-2-(4-methoxyphenyl)-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]oxymethyl]-5-hydroxy-2-(4-methoxyphenyl)-1,3-dioxan-4-yl]methyl]-7,8-dimethylbenzo[g]pteridine-2,4-dione
  参考文献：
  名称：

  Chemical synthesis of lampteroflavin as light emitter in the luminous mushroom, lampteromyces japonicus

  摘要：

  The synthesis of lampteroflavin (the light emitter of the luminous mushroom, Lampteromyces japonicus) is described. Protected riboflavin was stereoselectively glycosylated with ribofuranosyl imidate to give largely the alpha-product. Chloroethyl group which could be removed under neutral condition contributed to this synthesis.

  DOI：

  10.1016/s0040-4020(01)86553-4