(E)-1-[3-tert-butyldimethylsilyloxy-5-O-(2,3,4-tri-O-acetyl-β-D-glucopyranoside)phenyl]-2-(4'-tert-butyldimethylsilyloxyphenyl)ethene methyl ester | 1185745-14-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-1-[3-tert-butyldimethylsilyloxy-5-O-(2,3,4-tri-O-acetyl-β-D-glucopyranoside)phenyl]-2-(4'-tert-butyldimethylsilyloxyphenyl)ethene methyl ester
• 英文别名: methyl (2S,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-[3-[tert-butyl(dimethyl)silyl]oxy-5-[(E)-2-[4-[tert-butyl(dimethyl)silyl]oxyphenyl]ethenyl]phenoxy]oxane-2-carboxylate
• CAS: 1185745-14-5
• 化学式: C₃₉H₅₆O₁₂Si₂
• 分子量: 773.037
• InChiKey: IGMZVPCGZPFTPR-ZYVAQBSUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  53
• 可旋转键数：
  18
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  142
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  (E)-1-[3-tert-butyldimethylsilyloxy-5-O-(2,3,4-tri-O-acetyl-β-D-glucopyranoside)phenyl]-2-(4'-tert-butyldimethylsilyloxyphenyl)ethene methyl ester 在 吡啶 、 氢氟酸 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以80%的产率得到
  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：

  (E)-1-{[3-tert-butyl(dimethyl)silyl]oxy}-5-hydroxyphenyl-2-({[4-tert-butyl(dimethyl)silyl]oxy}-phenyl)ethene 、 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 1.5h， 以71%的产率得到(E)-1-[3-tert-butyldimethylsilyloxy-5-O-(2,3,4-tri-O-acetyl-β-D-glucopyranoside)phenyl]-2-(4'-tert-butyldimethylsilyloxyphenyl)ethene methyl ester
  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