3-benzyloxy-4-(2',3',4',6'-tetra-O-benzyl-β-D-glucopyranosyloxy)benzoic acid

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 单宁
• 英文名称: 3-benzyloxy-4-(2',3',4',6'-tetra-O-benzyl-β-D-glucopyranosyloxy)benzoic acid
• 英文别名: 3-phenylmethoxy-4-[(2S,3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxybenzoic acid
• 化学式: C₄₈H₄₆O₉
• 分子量: 767.877
• InChiKey: GNDBNMKFTOWLDH-OAAKKQBPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  57
• 可旋转键数：
  19
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2-hydroxy-ω,4,6-tribenzyloxyacetophenone 、 3-benzyloxy-4-(2',3',4',6'-tetra-O-benzyl-β-D-glucopyranosyloxy)benzoic acid 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以68%的产率得到[3,5-bis(phenylmethoxy)-2-(2-phenylmethoxyacetyl)phenyl] 3-phenylmethoxy-4-[(2S,3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxybenzoate
  参考文献：
  名称：

  Isotopic Labelling of Quercetin 4′-O-β-d-Glucoside

  摘要：

  [2-C-13]-Quercetin-4'-O-beta-glucoside was synthesised in four steps and 28% yield from barium [C-13]-carbonate. This short route will be applicable to the synthesis of radiolabelled quercetin-4'-O-beta-D-glucoside from barium [C-14]-carbonate. The most important feature is control of the regiochemistry and stereochemistry of glycosylation before introduction of the isotopic label. The synthesis also uses only benzyl protecting groups allowing global deprotection in the last step. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00325-2
• 作为产物：
  描述：

  二氧化碳-13C 、 1-iodo-3-benzyloxy-4-(2',3',4',6'-tetra-O-benzyl-β-D-glucopyranosyloxy)benzene 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， -78.0 ℃ 、28.0 kPa 条件下， 反应 0.5h， 生成 3-benzyloxy-4-(2',3',4',6'-tetra-O-benzyl-β-D-glucopyranosyloxy)benzoic acid
  参考文献：
  名称：

  Isotopic Labelling of Quercetin 4′-O-β-d-Glucoside

  摘要：

  [2-C-13]-Quercetin-4'-O-beta-glucoside was synthesised in four steps and 28% yield from barium [C-13]-carbonate. This short route will be applicable to the synthesis of radiolabelled quercetin-4'-O-beta-D-glucoside from barium [C-14]-carbonate. The most important feature is control of the regiochemistry and stereochemistry of glycosylation before introduction of the isotopic label. The synthesis also uses only benzyl protecting groups allowing global deprotection in the last step. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00325-2

文献信息

• Isotopic Labelling of Quercetin 4′-O-β-d-Glucoside
  作者：Stuart T Caldwell、Alan Crozier、Richard C Hartley

  DOI：10.1016/s0040-4020(00)00325-2

  日期：2000.6

  [2-C-13]-Quercetin-4'-O-beta-glucoside was synthesised in four steps and 28% yield from barium [C-13]-carbonate. This short route will be applicable to the synthesis of radiolabelled quercetin-4'-O-beta-D-glucoside from barium [C-14]-carbonate. The most important feature is control of the regiochemistry and stereochemistry of glycosylation before introduction of the isotopic label. The synthesis also uses only benzyl protecting groups allowing global deprotection in the last step. (C) 2000 Elsevier Science Ltd. All rights reserved.