6,8-di-C-β-D-glucopyranosylnaringenin | 898278-67-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 6,8-di-C-β-D-glucopyranosylnaringenin
• 英文别名: 5,7-dihydroxy-2-(4-hydroxyphenyl)-6,8-bis[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-2,3-dihydrochromen-4-one
• CAS: 898278-67-6
• 化学式: C₂₇H₃₂O₁₅
• 分子量: 596.542
• InChiKey: KLDARLGFVGIIIL-NZCHJKHZSA-N

物化性质

• 沸点：
  989.8±65.0 °C(predicted)
• 密度：
  1.719±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.5
• 重原子数：
  42
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  267
• 氢给体数：
  11
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  6,8-di-C-β-D-glucopyranosylnaringenin 、 乙酸酐 在 吡啶 作用下， 以44%的产率得到[(2R,3R,4R,5S,6S)-3,4,5-triacetyloxy-6-[(2R)-5,7-diacetyloxy-2-(4-acetyloxyphenyl)-4-oxo-6-[(2S,3S,4R,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]-2,3-dihydrochromen-8-yl]oxan-2-yl]methyl acetate
  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：

  4-苄氧基苯甲醛 在 盐酸 、 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 25.25h， 生成 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

文献信息

• WO2023/198436
  申请人：——

  公开号：——

  公开（公告）日：——
• 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.