N(2)-acetyl-6-[(2,3,4,6-tetra-O-acetyl-β-D-glycopyranosyloxy)methyl]pterin | 1225517-27-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N(2)-acetyl-6-[(2,3,4,6-tetra-O-acetyl-β-D-glycopyranosyloxy)methyl]pterin
• CAS: 1225517-27-0
• 化学式: C₂₃H₂₇N₅O₁₂
• 分子量: 565.494
• InChiKey: MKCHKSKVGFJSNO-DRASZATQSA-N

反应信息

• 作为反应物：
  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
• 作为产物：
  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