Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-(3-formyl-phenoxy)-tetrahydro-pyran-3-yl ester | 403822-04-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-(3-formyl-phenoxy)-tetrahydro-pyran-3-yl ester
• CAS: 403822-04-8
• 化学式: C₂₁H₂₄O₁₁
• 分子量: 452.415
• InChiKey: IUXUNKKLJNQEFC-XDWAVFMPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.96
• 重原子数：
  32.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  140.73
• 氢给体数：
  0.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  吡咯 、 Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-(3-formyl-phenoxy)-tetrahydro-pyran-3-yl ester 在 三氟化硼乙醚 、 zinc diacetate 、 四氯苯醌 作用下， 以 氯仿 为溶剂， 反应 25.0h， 生成 [5,10,15,20-tetrakis[3-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyloxy)phenyl]porphyrinato]zinc(II)
  参考文献：
  名称：

  Cellular Uptake and Photocytotoxicity of Glycoconjugated Porphyrins in HeLa Cells¶

  摘要：

  Thirty-two glycoconjugated porphyrins were synthesized by a modification of Lindsey method in the presence of Zn(OAc)(2).2H(2)O as a template. The Zn2+ ion template strategy improved the yield about three-fold in the case of meta-substituted tetraphenylporphyrins. In addition, free-base porphyrins were obtained almost quantitatively by demetalation with 4 M HCl. Sixteen deacetylated glycoconjugated porphyrins were tested as candidate photodynamic therapy (PDT) drugs using HeLa cells. Most of the deacetylated glycoconjugated porphyrins showed higher cellular uptake than tetraphenylporphyrin tetrasulfonic acid (TPPS), and 5,10,15, 20-tetrakis[4-(beta-D-arabinopyranosyloxy)phenyl]porphyrin (p-5d) in particular showed 18.5-fold higher uptake than TPPS. The photocytotoxicity of 5,10,15,20-tetrakis[4-(beta-D-glucopyranosyloxy)phenyl]porphyrin (p-5a), p-5d and TPPS was examined with HeLa cells, using a light dose of 16 J/cm(2). These photosensitizers had no cytotoxicity in the dark, but their photocytotoxicity increased in the order of TPPS < p-5a < p-5d. These results suggest p-5d is a good candidate for a PDT drug.

  DOI：

  10.1562/2004-03-07-ra-103.1
• 作为产物：
  描述：

  1-bromo-2,3,4,6-tetra-O-acetyl-D-galactopyranose 、 间羟基苯甲醛 以50%的产率得到Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-(3-formyl-phenoxy)-tetrahydro-pyran-3-yl ester
  参考文献：
  名称：

  Cellular Uptake and Photocytotoxicity of Glycoconjugated Porphyrins in HeLa Cells¶

  摘要：

  Thirty-two glycoconjugated porphyrins were synthesized by a modification of Lindsey method in the presence of Zn(OAc)(2).2H(2)O as a template. The Zn2+ ion template strategy improved the yield about three-fold in the case of meta-substituted tetraphenylporphyrins. In addition, free-base porphyrins were obtained almost quantitatively by demetalation with 4 M HCl. Sixteen deacetylated glycoconjugated porphyrins were tested as candidate photodynamic therapy (PDT) drugs using HeLa cells. Most of the deacetylated glycoconjugated porphyrins showed higher cellular uptake than tetraphenylporphyrin tetrasulfonic acid (TPPS), and 5,10,15, 20-tetrakis[4-(beta-D-arabinopyranosyloxy)phenyl]porphyrin (p-5d) in particular showed 18.5-fold higher uptake than TPPS. The photocytotoxicity of 5,10,15,20-tetrakis[4-(beta-D-glucopyranosyloxy)phenyl]porphyrin (p-5a), p-5d and TPPS was examined with HeLa cells, using a light dose of 16 J/cm(2). These photosensitizers had no cytotoxicity in the dark, but their photocytotoxicity increased in the order of TPPS < p-5a < p-5d. These results suggest p-5d is a good candidate for a PDT drug.

  DOI：

  10.1562/2004-03-07-ra-103.1