N(2)-(N,N-dimethylaminomethylene)-3-[2-(4-nitrophenyl)ethyl]-6-[(2,3,4,6-tetra-O-benzoyl-β-D-glycopyranosyloxy)methyl]pterin | 1225517-14-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N(2)-(N,N-dimethylaminomethylene)-3-[2-(4-nitrophenyl)ethyl]-6-[(2,3,4,6-tetra-O-benzoyl-β-D-glycopyranosyloxy)methyl]pterin
• CAS: 1225517-14-5
• 化学式: C₅₂H₄₅N₇O₁₃
• 分子量: 975.968
• InChiKey: MLASVBOHFAQYMP-KSPMRNABSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.33
• 重原子数：
  72.0
• 可旋转键数：
  18.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  243.07
• 氢给体数：
  0.0
• 氢受体数：
  18.0

反应信息

• 作为反应物：
  描述：

  N(2)-(N,N-dimethylaminomethylene)-3-[2-(4-nitrophenyl)ethyl]-6-[(2,3,4,6-tetra-O-benzoyl-β-D-glycopyranosyloxy)methyl]pterin 在 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Synthesis of 6-Hydroxymethylpterin α- and β-D-Glucosides

  摘要：

  The key precursor, N(2)-(N,N-dimethylaminomethylene)-6-hydroxymethyl-3-[2-(4-nitrophenyl)ethyl]pterin (11) was efficiently prepared from 2,5,6-triamino-4-hydroxypyrimidine (8) in 5 steps. The first, unequivocal synthesis of 6-hydroxymethylpterin alpha-D-glucoside (6a) was achieved by treatment of 11 with 4,6-di-O-acetyl-2,3-di-O-(4-methoxybenzyl)-alpha-D-glucopyranosyl bromide (16) in the presence of tetraethylammonium bromide and N-ethyldiisopropylamine, followed by removal of the protecting groups, while 6-hydroxymethylpterin beta-D-glucoside (6b) was prepared by means of selective glycosylation of 11 with 2,3,4,6-tetra-O-benzoyl-alpha-D-glucopyranosyl bromide (12) in the presence of silver triflate and tetramethylurea.

  DOI：

  10.3987/com-09-s(s)78
• 作为产物：
  描述：

  2,3,4,6-tetra-O-benzoylglucosyl bromide 、 N(2)-(N,N-dimethylaminomethylene)-6-hydroxymethyl-3-[2-(4-nitrophenyl)ethyl]pterin 在 silver trifluoromethanesulfonate 、 1,1,3,3-四甲基脲 作用下， 以 氯仿 为溶剂， 反应 6.0h， 以63%的产率得到N(2)-(N,N-dimethylaminomethylene)-3-[2-(4-nitrophenyl)ethyl]-6-[(2,3,4,6-tetra-O-benzoyl-β-D-glycopyranosyloxy)methyl]pterin
  参考文献：
  名称：

  Synthesis of 6-Hydroxymethylpterin α- and β-D-Glucosides

  摘要：

  The key precursor, N(2)-(N,N-dimethylaminomethylene)-6-hydroxymethyl-3-[2-(4-nitrophenyl)ethyl]pterin (11) was efficiently prepared from 2,5,6-triamino-4-hydroxypyrimidine (8) in 5 steps. The first, unequivocal synthesis of 6-hydroxymethylpterin alpha-D-glucoside (6a) was achieved by treatment of 11 with 4,6-di-O-acetyl-2,3-di-O-(4-methoxybenzyl)-alpha-D-glucopyranosyl bromide (16) in the presence of tetraethylammonium bromide and N-ethyldiisopropylamine, followed by removal of the protecting groups, while 6-hydroxymethylpterin beta-D-glucoside (6b) was prepared by means of selective glycosylation of 11 with 2,3,4,6-tetra-O-benzoyl-alpha-D-glucopyranosyl bromide (12) in the presence of silver triflate and tetramethylurea.

  DOI：

  10.3987/com-09-s(s)78