1-(p-benzyloxy)cinnamoyl-2,4,6-tribenzyloxy-3,5-di-C-β-D-glucopyranosylbenzene | 897935-58-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(p-benzyloxy)cinnamoyl-2,4,6-tribenzyloxy-3,5-di-C-β-D-glucopyranosylbenzene
• 英文别名: (E)-3-(4-phenylmethoxyphenyl)-1-[2,4,6-tris(phenylmethoxy)-3,5-bis[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]phenyl]prop-2-en-1-one
• CAS: 897935-58-9
• 化学式: C₅₅H₅₆O₁₅
• 分子量: 957.041
• InChiKey: HIVKNOBUSLDVMX-KCJPUVGVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  70
• 可旋转键数：
  19
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  234
• 氢给体数：
  8
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  1-(p-benzyloxy)cinnamoyl-2,4,6-tribenzyloxy-3,5-di-C-β-D-glucopyranosylbenzene 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 甲醇 为溶剂， 反应 1.25h， 以98%的产率得到6,8-di-C-β-D-glucopyranosylnaringenin
  参考文献：
  名称：

  Total synthesis of three naturally occurring 6,8-di-C-glycosylflavonoids: phloretin, naringenin, and apigenin bis-C-β-d-glucosides

  摘要：

  Three naturally occurring di-C-glycosylflavonoids, phloretin (dihydrochalcone), naringenin (flavanone), and apigenin (flavone) bis-6,8-C-beta-D-glucopyranosides (4, 5, and 6), were synthesized in total yields of 52.3%, 53.5%, and 36.4%, respectively, starting from the key compound, di-C-beta-D-glucopyranosylphloroacetophenone (1). Benzyl protection of the phenolic hydroxyls in I and a subsequent aldol condensation with benzyloxybenzaldehyde led to the production of chalcone 3, which, after hydrogenolysis or acid hydrolysis and deprotection, gave 4 and 5, respectively. The acetylation of 5, followed by DDQ oxidation and deprotection, gave 6. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.02.019
• 作为产物：
  描述：

  2,4,6-trihydroxyacetophenone-3,5-di-C-glucoside 在 氢氧化钾 、 potassium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 1-(p-benzyloxy)cinnamoyl-2,4,6-tribenzyloxy-3,5-di-C-β-D-glucopyranosylbenzene
  参考文献：
  名称：

  Total synthesis of three naturally occurring 6,8-di-C-glycosylflavonoids: phloretin, naringenin, and apigenin bis-C-β-d-glucosides

  摘要：

  Three naturally occurring di-C-glycosylflavonoids, phloretin (dihydrochalcone), naringenin (flavanone), and apigenin (flavone) bis-6,8-C-beta-D-glucopyranosides (4, 5, and 6), were synthesized in total yields of 52.3%, 53.5%, and 36.4%, respectively, starting from the key compound, di-C-beta-D-glucopyranosylphloroacetophenone (1). Benzyl protection of the phenolic hydroxyls in I and a subsequent aldol condensation with benzyloxybenzaldehyde led to the production of chalcone 3, which, after hydrogenolysis or acid hydrolysis and deprotection, gave 4 and 5, respectively. The acetylation of 5, followed by DDQ oxidation and deprotection, gave 6. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.02.019

文献信息

• Total synthesis of three naturally occurring 6,8-di-C-glycosylflavonoids: phloretin, naringenin, and apigenin bis-C-β-d-glucosides
  作者：Shingo Sato、Toshiki Akiya、Hiroaki Nishizawa、Toshiyuki Suzuki

  DOI：10.1016/j.carres.2006.02.019

  日期：2006.6

  Three naturally occurring di-C-glycosylflavonoids, phloretin (dihydrochalcone), naringenin (flavanone), and apigenin (flavone) bis-6,8-C-beta-D-glucopyranosides (4, 5, and 6), were synthesized in total yields of 52.3%, 53.5%, and 36.4%, respectively, starting from the key compound, di-C-beta-D-glucopyranosylphloroacetophenone (1). Benzyl protection of the phenolic hydroxyls in I and a subsequent aldol condensation with benzyloxybenzaldehyde led to the production of chalcone 3, which, after hydrogenolysis or acid hydrolysis and deprotection, gave 4 and 5, respectively. The acetylation of 5, followed by DDQ oxidation and deprotection, gave 6. (c) 2006 Elsevier Ltd. All rights reserved.