[(2R,3R,4S,5R,6S)-3-hydroxy-2-(hydroxymethyl)-5,6-bis[(3,4,5-trimethoxybenzoyl)oxy]oxan-4-yl] 3,4,5-trimethoxybenzoate | 158847-08-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 单宁
• 英文名称: [(2R,3R,4S,5R,6S)-3-hydroxy-2-(hydroxymethyl)-5,6-bis[(3,4,5-trimethoxybenzoyl)oxy]oxan-4-yl] 3,4,5-trimethoxybenzoate
• CAS: 158847-08-6
• 化学式: C₃₆H₄₂O₁₈
• 分子量: 762.719
• InChiKey: VZPCLGCCNHPGOT-FKBDFFMGSA-N

物化性质

• 沸点：
  782.4±60.0 °C(predicted)
• 密度：
  1.40±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  54
• 可旋转键数：
  19
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  212
• 氢给体数：
  2
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  [(2R,3R,4S,5R,6S)-3-hydroxy-2-(hydroxymethyl)-5,6-bis[(3,4,5-trimethoxybenzoyl)oxy]oxan-4-yl] 3,4,5-trimethoxybenzoate 、 (S)-4,4',5,5',6,6'-hexamethoxybiphenyl-2,2'-dicarboxylic acid 在 4-二甲氨基吡啶 、 4-(dimethylamino)pyridine hydrochloride 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以77%的产率得到β-1,2,3-tri-O-galloyl-4,6-(S)-hexahydroxydiphenoyl-D-glucose pentadecamethyl ether
  参考文献：
  名称：

  Cyanocuprate-mediated intramolecular biaryl couplings applied to an ellagitannin. Synthesis of (+)-O-permethyltellimagrandin II

  摘要：

  Generation of an intramolecularly tethered, nonracemic diaryl cuprate followed by its oxidation with ground state oxygen at -78 degrees leads to a biaryl precursor to an ellagitannin. Subsequent attachment of the appropriate glucose unit completes the synthesis of the title compound.

  DOI：

  10.1016/s0040-4039(00)77248-0
• 作为产物：
  描述：

  可得然胶 在 oxonium 、 氢气 作用下， 以 水 为溶剂， 生成 [(2R,3R,4S,5R,6S)-3-hydroxy-2-(hydroxymethyl)-5,6-bis[(3,4,5-trimethoxybenzoyl)oxy]oxan-4-yl] 3,4,5-trimethoxybenzoate
  参考文献：
  名称：

  Cyanocuprate-mediated intramolecular biaryl couplings applied to an ellagitannin. Synthesis of (+)-O-permethyltellimagrandin II

  摘要：

  Generation of an intramolecularly tethered, nonracemic diaryl cuprate followed by its oxidation with ground state oxygen at -78 degrees leads to a biaryl precursor to an ellagitannin. Subsequent attachment of the appropriate glucose unit completes the synthesis of the title compound.

  DOI：

  10.1016/s0040-4039(00)77248-0

文献信息

• NONAKA, GEN-ICHIRO;ISHIMATSU, MAKOTO;TANAKA, TAKASHI;NISHIOKA, ITSUO;NISH+, CHEM. AND PHARM. BULL., 35,(1987) N 8, 3127-3131
  作者：NONAKA, GEN-ICHIRO、ISHIMATSU, MAKOTO、TANAKA, TAKASHI、NISHIOKA, ITSUO、NISH+

  DOI：——

  日期：——
• Cyanocuprate-mediated intramolecular biaryl couplings applied to an ellagitannin. Synthesis of (+)-O-permethyltellimagrandin II
  作者：Bruce H. Lipshutz、Zi-Ping Liu、Frank Kayser

  DOI：10.1016/s0040-4039(00)77248-0

  日期：1994.8

  Generation of an intramolecularly tethered, nonracemic diaryl cuprate followed by its oxidation with ground state oxygen at -78 degrees leads to a biaryl precursor to an ellagitannin. Subsequent attachment of the appropriate glucose unit completes the synthesis of the title compound.