allyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->2)-3,4,6-tri-O-benzoyl-β-D-glucopyranoside | 677766-80-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->2)-3,4,6-tri-O-benzoyl-β-D-glucopyranoside
• CAS: 677766-80-2
• 化学式: C₆₄H₅₄O₁₈
• 分子量: 1111.12
• InChiKey: XAIRXCHZSOQQSY-HGIUFAEVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.87
• 重原子数：
  82.0
• 可旋转键数：
  21.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  221.02
• 氢给体数：
  0.0
• 氢受体数：
  18.0

反应信息

• 作为反应物：
  描述：

  allyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->2)-3,4,6-tri-O-benzoyl-β-D-glucopyranoside 在 sodium acetate 、 溶剂黄146 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 palladium dichloride 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->2)-3,4,6-tri-O-benzoyl-D-glucopyranosyl trichloroacetimidate
  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：

  allyl 3,4,6-tri-O-benzoyl-β-D-glucopyranoside 、 2,3,4,6-tetra-O-benzoyl-D-glucopyranosyl trichloroacetimidate 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以90%的产率得到allyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->2)-3,4,6-tri-O-benzoyl-β-D-glucopyranoside
  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