2-{4-[(2-Amino-4-oxo-3,4-dihydro-pteridin-6-ylmethyl)-(2,2,2-trifluoro-acetyl)-amino]-benzoylamino}-pentanedioic acid

• 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: 2-{4-[(2-Amino-4-oxo-3,4-dihydro-pteridin-6-ylmethyl)-(2,2,2-trifluoro-acetyl)-amino]-benzoylamino}-pentanedioic acid
• 英文别名: Unk-N(Tfa)4Abz-DL-Glu-OH；2-[[4-[(2-amino-4-oxo-3H-pteridin-6-yl)methyl-(2,2,2-trifluoroacetyl)amino]benzoyl]amino]pentanedioic acid
• 化学式: C₂₁H₁₈F₃N₇O₇
• 分子量: 537.412
• InChiKey: JMJXGSZJTKQYNO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  38
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  217
• 氢给体数：
  5
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  L-谷氨酸 在 盐酸 、 1,1,2,3-四甲基胍 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 反应 22.5h， 生成 2-{4-[(2-Amino-4-oxo-3,4-dihydro-pteridin-6-ylmethyl)-(2,2,2-trifluoro-acetyl)-amino]-benzoylamino}-pentanedioic acid
  参考文献：
  名称：

  Efficient Syntheses of Pyrofolic Acid and Pteroyl Azide, Reagents for the Production of Carboxyl-Differentiated Derivatives of Folic Acid

  摘要：

  Reaction of folic acid (1) with excess trifluoroacetic anhydride provides access to both the previously unknown N-10-(trifluoroacetyl)pyrofolic acid (8) and pyrofolic acid (9). Reaction of either of these materials with hydrazine selectively affords pteroyl hydrazide (13), which may be oxidized to pteroyl azide (27) on a large scale (62% overall from 1 without the need for chromatography). Treatment of 27 with differentially protected glutamates provides a convenient and high-yielding synthesis of differentially protected, optically pure folates.

  DOI：

  10.1021/ja971568j

文献信息

• Efficient Syntheses of Pyrofolic Acid and Pteroyl Azide, Reagents for the Production of Carboxyl-Differentiated Derivatives of Folic Acid
  作者：Jin Luo、Michael D. Smith、Douglas A. Lantrip、Susan Wang、P. L. Fuchs

  DOI：10.1021/ja971568j

  日期：1997.10.1

  Reaction of folic acid (1) with excess trifluoroacetic anhydride provides access to both the previously unknown N-10-(trifluoroacetyl)pyrofolic acid (8) and pyrofolic acid (9). Reaction of either of these materials with hydrazine selectively affords pteroyl hydrazide (13), which may be oxidized to pteroyl azide (27) on a large scale (62% overall from 1 without the need for chromatography). Treatment of 27 with differentially protected glutamates provides a convenient and high-yielding synthesis of differentially protected, optically pure folates.