5,7-bis(benzyloxy)-3-(3,4,6-tri-O-benzyl-β-D-glucopyranosyl)-2-[3,4-bis(benzyloxy)phenyl]-5-hydroxy-4H-1-benzopyran-4-one | 677766-61-9

• 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: 5,7-bis(benzyloxy)-3-(3,4,6-tri-O-benzyl-β-D-glucopyranosyl)-2-[3,4-bis(benzyloxy)phenyl]-5-hydroxy-4H-1-benzopyran-4-one
• 英文别名: 2-[3,4-bis(phenylmethoxy)phenyl]-3-[(2S,3R,4R,5R,6R)-3-hydroxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxy-5,7-bis(phenylmethoxy)chromen-4-one
• CAS: 677766-61-9
• 化学式: C₇₀H₆₂O₁₂
• 分子量: 1095.26
• InChiKey: LKUNIWKKROBXKX-OFSKKIBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.6
• 重原子数：
  82
• 可旋转键数：
  25
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  130
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  3,4,6-tri-O-benzyl-2-O-acetyl-α-D-glucosyl trichloroimidate 、 5,7-bis(benzyloxy)-3-(3,4,6-tri-O-benzyl-β-D-glucopyranosyl)-2-[3,4-bis(benzyloxy)phenyl]-5-hydroxy-4H-1-benzopyran-4-one 在 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以87%的产率得到5,7-bis(benzyloxy)-3-[2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl-(1->2)-3,4,6-tri-O-benzyl-β-D-glucopyranosyl]-2-[3,4-bis(benzyloxy)phenyl]-5-hydroxy-4H-1-benzopyran-4-one
  参考文献：
  名称：

  Total Synthesis of Quercetin 3-Sophorotrioside

  摘要：

  5,7-Dihydroxy-3-[beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranosyl]-2-(3,4-dihydroxy- phenyl)-4H-1-benzopyran-4-one (quercetin 3-sophorotrioside), a flavonol triglycoside, isolated from Pisum sativurn shoots and showing protective effects on liver injury induced by chemicals, was synthesized for the first time. The target compound was successfully synthesized in eight linear steps and in 39% overall yield through a combination of phasetransfer-catalyzed (PTC) quercetin C-3 glycosylation and silver triflate (AgOTf) promoted carbohydrate chain elongation using both sugar bromide and trichloroacetimidate donors.

  DOI：

  10.1021/jo035722y
• 作为产物：
  描述：

  5,7-bis(benzyloxy)-3-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl)-2-[3,4-bis(benzyloxy)phenyl]-5-hydroxy-4H-1-benzopyran-4-one 在 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 16.0h， 以86%的产率得到5,7-bis(benzyloxy)-3-(3,4,6-tri-O-benzyl-β-D-glucopyranosyl)-2-[3,4-bis(benzyloxy)phenyl]-5-hydroxy-4H-1-benzopyran-4-one
  参考文献：
  名称：

  Total Synthesis of Quercetin 3-Sophorotrioside

  摘要：

  5,7-Dihydroxy-3-[beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranosyl]-2-(3,4-dihydroxy- phenyl)-4H-1-benzopyran-4-one (quercetin 3-sophorotrioside), a flavonol triglycoside, isolated from Pisum sativurn shoots and showing protective effects on liver injury induced by chemicals, was synthesized for the first time. The target compound was successfully synthesized in eight linear steps and in 39% overall yield through a combination of phasetransfer-catalyzed (PTC) quercetin C-3 glycosylation and silver triflate (AgOTf) promoted carbohydrate chain elongation using both sugar bromide and trichloroacetimidate donors.

  DOI：

  10.1021/jo035722y