tert-butyldimethylsilyl 3-(tert-butyldimethylsilyl)-4,5-(diphenylmethylenedioxy)benzoate | 146322-16-9

• 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: tert-butyldimethylsilyl 3-(tert-butyldimethylsilyl)-4,5-(diphenylmethylenedioxy)benzoate
• CAS: 146322-16-9
• 化学式: C₃₂H₄₂O₅Si₂
• 分子量: 562.853
• InChiKey: COVYKBVUOUOCHB-UHFFFAOYSA-N

物化性质

• 沸点：
  564.0±50.0 °C(predicted)
• 密度：
  1.070±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.91
• 重原子数：
  39.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  53.99
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  tert-butyldimethylsilyl 3-(tert-butyldimethylsilyl)-4,5-(diphenylmethylenedioxy)benzoate 在 palladium on activated charcoal 4-二甲氨基吡啶 、 四丁基氟化铵 、 氢气 、 4-(dimethylamino)pyridine hydrochloride 、 溶剂黄146 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 22.0h， 生成 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：

  没食子酸甲酯 在 lithium hydroxide 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 tert-butyldimethylsilyl 3-(tert-butyldimethylsilyl)-4,5-(diphenylmethylenedioxy)benzoate
  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. Preparative and Mechanistic Studies of the Biomimetic Oxidative Coupling of Galloyl Esters
  作者：Ken S. Feldman、Susan M. Ensel

  DOI：10.1021/ja00087a022

  日期：1994.4

  The construction of strictly the (S)-hexahydroxydiphenyl (HHDP) unit via biomimetic cyclization of suitably protected glucose-derived digalloyl esters has been achieved in good yield. Studies on substrates of increasing complexity utilizing a range of oxidants (Pb(OAc)(4), VOF3, Tl2O3) have helped define the scope and limitations of this approach to ellagitannin synthesis. Computer modeling of key cyclization precursors helped elucidate the molecular-level structural details which undergird the Haslam/Schmidt biosynthesis model for this class of naturally occurring secondary plant metabolites.