methyl [1-(dibenzo[b,d]pyranyl-6-one)]-2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate | 1185745-11-2

• 分子结构分类: 有机化合物
• 英文名称: methyl [1-(dibenzo[b,d]pyranyl-6-one)]-2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate
• 英文别名: methyl (2S,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-(6-oxobenzo[c]chromen-3-yl)oxyoxane-2-carboxylate
• CAS: 1185745-11-2
• 化学式: C₂₆H₂₄O₁₂
• 分子量: 528.469
• InChiKey: WEVUTCSPZAXWFO-MPJDBJFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.02
• 重原子数：
  38.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  153.87
• 氢给体数：
  0.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  methyl [1-(dibenzo[b,d]pyranyl-6-one)]-2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate 在 水 、 sodium carbonate 作用下， 以 甲醇 为溶剂， 反应 5.0h， 以83%的产率得到sodium 1-(dibenzo[b,d]pyranyl-6-one)-β-D-glucopyranosyluronic acid
  参考文献：
  名称：

  A concise synthesis of glucuronide metabolites of urolithin-B, resveratrol, and hydroxytyrosol

  摘要：

  A simple and direct strategy to chemically synthesize O-beta-D-glucuronides of urolithin-B 4, resveratrol 5, and the corresponding hydroxytyrosol derivatives 6, 7 (as a regioisomeric mixture), and 8 is described. The critical glycosylation step has been optimized using a structurally simple phenol, urolithin-B, by modification of several reaction parameters (solvent, promoter, and glucuronide donor). Very high yields have been obtained in the first synthesis of the O-beta-D-glucuronide of urolithin-B 4. Extension of these reaction conditions was used for the synthesis of resveratrol-3-O-glucuronide 5 where a higher yield than previously reported was obtained by using the much more common trichloroacetimidate glucuronide donor. Finally, three O-beta-D-glucuronides of hydroxytyrosol 6, 7, and 8 have been synthesized for the first time using chemical synthesis. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2009.05.016
• 作为产物：
  描述：

  尿石素B 、 methyl 2,3,4-tri-O-acetyl-α,β-D-glucopyranosyluronate trichloroacetimidate 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以95%的产率得到methyl [1-(dibenzo[b,d]pyranyl-6-one)]-2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate
  参考文献：
  名称：

  A concise synthesis of glucuronide metabolites of urolithin-B, resveratrol, and hydroxytyrosol

  摘要：

  A simple and direct strategy to chemically synthesize O-beta-D-glucuronides of urolithin-B 4, resveratrol 5, and the corresponding hydroxytyrosol derivatives 6, 7 (as a regioisomeric mixture), and 8 is described. The critical glycosylation step has been optimized using a structurally simple phenol, urolithin-B, by modification of several reaction parameters (solvent, promoter, and glucuronide donor). Very high yields have been obtained in the first synthesis of the O-beta-D-glucuronide of urolithin-B 4. Extension of these reaction conditions was used for the synthesis of resveratrol-3-O-glucuronide 5 where a higher yield than previously reported was obtained by using the much more common trichloroacetimidate glucuronide donor. Finally, three O-beta-D-glucuronides of hydroxytyrosol 6, 7, and 8 have been synthesized for the first time using chemical synthesis. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2009.05.016