6-[(β-D-glucopyranosyloxy)methyl]pterin | 897946-35-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 蝶啶及其衍生物
• 英文名称: 6-[(β-D-glucopyranosyloxy)methyl]pterin
• 英文别名: 2-amino-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-3H-pteridin-4-one
• CAS: 897946-35-9
• 化学式: C₁₃H₁₇N₅O₇
• 分子量: 355.307
• InChiKey: JHXZDZLMCWPGJQ-GXIXWSSHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.8
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  193
• 氢给体数：
  6
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  6-[(β-D-glucopyranosyloxy)methyl]pterin 、 乙酸酐 在 吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以94%的产率得到N(2)-acetyl-6-[(2,3,4,6-tetra-O-acetyl-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
• 作为产物：
  描述：

  N(2)-acetyl-6-[(2,3,4,6-tetra-O-acetyl-β-D-glycopyranosyloxy)methyl]pterin 在 ammonium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 16.0h， 以92%的产率得到6-[(β-D-glucopyranosyloxy)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