methyl 4,6-O-benzylidene-2,3-bis(3,4-((diphenylmethylene)dioxy)-5-hydroxybenzoyl)-α-D-glucopyranoside | 869278-93-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 4,6-O-benzylidene-2,3-bis(3,4-((diphenylmethylene)dioxy)-5-hydroxybenzoyl)-α-D-glucopyranoside
• 英文别名: methyl 4,6-O-benzylidene-2,3-bis(3,4-[(diphenylmethylene)dioxy]-5-hydroxybenzoyl)-α-D-glucopyranoside
• CAS: 869278-93-3
• 化学式: C₅₄H₄₂O₁₄
• 分子量: 914.919
• InChiKey: LFKCAIUYDLBBLV-OMKBVQGTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.68
• 重原子数：
  68.0
• 可旋转键数：
  10.0
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  166.9
• 氢给体数：
  2.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  methyl 4,6-O-benzylidene-2,3-bis(3,4-((diphenylmethylene)dioxy)-5-hydroxybenzoyl)-α-D-glucopyranoside 在 palladium on activated charcoal 氢气 作用下， 以 四氢呋喃 为溶剂， 反应 17.0h， 以27%的产率得到methyl 2,3-di-O-galloyl-α-D-glucopyranoside
  参考文献：
  名称：

  O-Methylglucogalloyl esters: Synthesis and evaluation of their antimycotic activity

  摘要：

  The two anomers of O-methyl gluco-2,3-digalloyl esters were synthesized and their antimycotic activity toward yeasts of biomedical importance was evaluated. When used at subinhibitory concentration and regardless of stereochemistry at the anomeric carbon, these compounds enhance the antimycotic activity of Amphotericin B. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.06.037
• 作为产物：
  描述：

  3,4-(diphenylmethylenedioxy)-5-hydroxybenzoic acid 在 4-二甲氨基吡啶 、 四丁基氟化铵 、 4-(dimethylamino)pyridine hydrochloride 、 溶剂黄146 、 N,N-二异丙基乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 methyl 4,6-O-benzylidene-2,3-bis(3,4-((diphenylmethylene)dioxy)-5-hydroxybenzoyl)-α-D-glucopyranoside
  参考文献：
  名称：

  O-Methylglucogalloyl esters: Synthesis and evaluation of their antimycotic activity

  摘要：

  The two anomers of O-methyl gluco-2,3-digalloyl esters were synthesized and their antimycotic activity toward yeasts of biomedical importance was evaluated. When used at subinhibitory concentration and regardless of stereochemistry at the anomeric carbon, these compounds enhance the antimycotic activity of Amphotericin B. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.06.037

文献信息

• Ellagitannin Chemistry. The First Total Chemical Synthesis of an O(2),O(3)-Galloyl-Coupled Ellagitannin, Sanguiin H-5
  作者：Ken S. Feldman、Aruna Sambandam

  DOI：10.1021/jo00130a016

  日期：1995.12

  The biomimetic synthesis of sanguiin H-5 (1) was accomplished through the diastereoselective formation of the crucial biphenyl carbon-carbon bond between galloyl moieties at the O(2) and O(3) positions of an appropriately protected glucose-derived precursor. Furthermore, the beta-anomeric galloyl linkage was established with complete stereochemical control.