2-amino-3-(β-D-glucopyranosyloxy)-γ-oxobenzenebutanoic acid | 156913-43-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-amino-3-(β-D-glucopyranosyloxy)-γ-oxobenzenebutanoic acid
• 英文别名: α-deamino-3-(β-D-glucopyranosyloxy)kynurenine；4-(2-amino-3-hydroxyphenyl)-4-oxobutanoic acid O-β-D-glucoside；4-(2-Amino-3-hydroxyphenyl)-4-oxobutanoic acid O-glucoside；4-[2-amino-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-4-oxobutanoic acid
• CAS: 156913-43-8
• 化学式: C₁₆H₂₁NO₉
• 分子量: 371.344
• InChiKey: XEXCWFKGYJFAQK-LMXXTMHSSA-N

物化性质

• 沸点：
  701.6±60.0 °C(Predicted)
• 密度：
  1.560±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  180
• 氢给体数：
  6
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  methyl 4-(3-hydroxy-2-nitrophenyl)-4-oxobutanoate 在 palladium on activated charcoal silver imidazolate 、 氢气 、 sodium methylate 、 zinc(II) chloride 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 33.0h， 生成 2-amino-3-(β-D-glucopyranosyloxy)-γ-oxobenzenebutanoic acid
  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

文献信息

• Synthesis of Human Ultraviolet Filter Compounds:  <i>O</i>-β-<scp>d</scp>-Glucopyranosides of 3-Hydroxykynurenine and 2-Amino-3-hydroxy-γ-oxobenzenebutanoic Acid
  作者：Michael K. Manthey、Joanne F. Jamie、Roger J. W. Truscott

  DOI：10.1021/jo982321n

  日期：1999.5.1

  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.
• JPH083183A
  申请人：——

  公开号：JPH083183A

  公开（公告）日：1996-01-09
• Total Synthesis of α-Deamino-3-(β- d -glucopyranosyloxy)kynurenine
  作者：H.Keith Chenault、Jie Yang、Douglass F. Taber

  DOI：10.1016/s0040-4020(00)00285-4

  日期：2000.6

  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.