methyl 4-oxo-4-<2-amino-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)oxyphenyl>-2-butenoate | 224044-69-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 4-oxo-4-<2-amino-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)oxyphenyl>-2-butenoate
• 英文别名: 3-(4-methoxy-4-oxobutanoyl)-2-aminophenyl tetra-O-acetyl-β-D-glucopyranoside；methyl 4-[2-amino-3-[(2S,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyphenyl]-4-oxobutanoate
• CAS: 224044-69-3
• 化学式: C₂₅H₃₁NO₁₃
• 分子量: 553.52
• InChiKey: SFAICJMDZBNFDQ-HYOIWIKGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  39
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  193
• 氢给体数：
  1
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  methyl 4-oxo-4-<2-amino-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)oxyphenyl>-2-butenoate 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 4-[2-Amino-3-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-phenyl]-4-oxo-butyric acid methyl ester
  参考文献：
  名称：

  Synthesis of Human Ultraviolet Filter Compounds:  O-β-d-Glucopyranosides of 3-Hydroxykynurenine and 2-Amino-3-hydroxy-γ-oxobenzenebutanoic Acid

  摘要：

  The role of endogenous tryptophan-derived UV filters in aging lenses and in human cataract is becoming increasingly important. The two major UV filters found in the lenses of primates, the O-beta-D-glucopyranosides of 3-hydroxykynurenine and 2-amino-3-hydroxy-gamma-oxobenzenebutanoic acid, 1 and 2, were synthesized from the common benzoyl acrylate precursor 2-amino-3-hydroxybenzoylacrylic acid 10. Synthesis of compound 3, the alpha-N-acetyl derivative of 1, was achieved using coupling of 2-nitro-3-benzyloxyacetophenone 4 with the sodium salt of diethyl acetamidomalonate as a key step. This is the first reported synthesis of the lenticular glucopyranoside 2 and the N-acetyl compound 3.

  DOI：

  10.1021/jo982321n
• 作为产物：
  描述：

  methyl 4-(3-hydroxy-2-nitrophenyl)-4-oxobutanoate 在 palladium on activated charcoal silver imidazolate 、 氢气 、 zinc(II) chloride 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 19.0h， 生成 methyl 4-oxo-4-<2-amino-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)oxyphenyl>-2-butenoate
  参考文献：
  名称：

  Total Synthesis of α-Deamino-3-(β- d -glucopyranosyloxy)kynurenine

  摘要：

  alpha-Deamino-3-(beta-D-glucopyranosyloxy)krynurenine a yellow, fluorescent compound isolated from human lens, was synthesized in 8 steps (10% overall yield) from commercially available 3-methoxy-2-nitrobenzaldehyde. Key events included preparation and glucosylation of methyl 4-(3-hydroxy-2-nitrophenyl)-4-oxobutanoate followed by reduction of the nitro group and deprotection. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00285-4