2,4,6-tri-O-benzyl-3,5-di-C-β-D-glucopyranosyl-phloroacetophenone | 897935-57-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,4,6-tri-O-benzyl-3,5-di-C-β-D-glucopyranosyl-phloroacetophenone
• 英文别名: 1-[2,4,6-tris(phenylmethoxy)-3,5-bis[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]phenyl]ethanone
• CAS: 897935-57-8
• 化学式: C₄₁H₄₆O₁₄
• 分子量: 762.808
• InChiKey: SJUINXKAZXUFEG-QREKGTOFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  55
• 可旋转键数：
  14
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  225
• 氢给体数：
  8
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  2,4,6-tri-O-benzyl-3,5-di-C-β-D-glucopyranosyl-phloroacetophenone 在 palladium on activated charcoal 氢氧化钾 、 氢气 作用下， 以 甲醇 为溶剂， 反应 48.0h， 生成 3',5'-di-C-β-D-glucopyranosyl phloretin
  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：

  溴甲苯 、 2,4,6-trihydroxyacetophenone-3,5-di-C-glucoside 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以65%的产率得到2,4,6-tri-O-benzyl-3,5-di-C-β-D-glucopyranosyl-phloroacetophenone
  参考文献：
  名称：

  Total Synthesis of Two Isoflavone Bis-C-glycosides: Genistein and Orobol 6,8-Di-C-β-d-glucopyranosides

  摘要：

  本文描述了首次成功合成两种异黄酮双C-糖苷，分别为大豆苷和黄酮苷6,8-二C-β-d-葡萄糖苷，来源于氟代酮双C-糖苷，整体产率分别为27%和19%。该合成过程采用了四步反应：首先是未保护的D-葡萄糖与氟代酮的直接C-糖苷化；然后通过醛缩合合成查尔酮；接着通过氧化重排使用DIB和对甲苯磺酸合成醚；最后在不保护葡萄糖结构的情况下，使用HCl形成异黄酮环。

  DOI：

  10.1055/s-0030-1257859

文献信息

• Total Synthesis of Two Isoflavone Bis-C-glycosides: Genistein and Orobol 6,8-Di-C-β-d-glucopyranosides
  作者：Shingo Sato、Hidetoshi Ishikawa

  DOI：10.1055/s-0030-1257859

  日期：2010.9

  This paper describes the first successful synthesis of two isoflavone bis-C-glycosides, genistein and orobol 6,8-di-C-β-d-glucopyranosides from phloroacetophenone bis-C-glycoside in total yields of 27 and 19%, respectively, using a four-step reaction: direct C-glycosylation of phloroacetophenone with unprotected d-glucose; chalcone synthesis by aldol condensation; acetal synthesis by oxidative rearrangement using DIB and p-TsOH; and formation of the isoflavone ring using HCl, without protection of the glucose moiety.

  本文描述了首次成功合成两种异黄酮双C-糖苷，分别为大豆苷和黄酮苷6,8-二C-β-d-葡萄糖苷，来源于氟代酮双C-糖苷，整体产率分别为27%和19%。该合成过程采用了四步反应：首先是未保护的D-葡萄糖与氟代酮的直接C-糖苷化；然后通过醛缩合合成查尔酮；接着通过氧化重排使用DIB和对甲苯磺酸合成醚；最后在不保护葡萄糖结构的情况下，使用HCl形成异黄酮环。
• 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.