2'-acetoxy-3,4,4',6'-tetra(benzyloxy)-3'-C-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)chalcone | 898550-58-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 单宁
• 英文名称: 2'-acetoxy-3,4,4',6'-tetra(benzyloxy)-3'-C-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)chalcone
• CAS: 898550-58-8
• 化学式: C₇₉H₇₂O₁₂
• 分子量: 1213.43
• InChiKey: KMIOGBHBMKZUIT-JQDWQWCASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.24
• 重原子数：
  91.0
• 可旋转键数：
  30.0
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  126.44
• 氢给体数：
  0.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  2'-acetoxy-3,4,4',6'-tetra(benzyloxy)-3'-C-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)chalcone 在 palladium dihydroxide thallium(III) nitrate 、 盐酸 、 氢气 作用下， 以 甲醇 、 1,4-二氧六环 、 乙酸乙酯 为溶剂， 反应 50.0h， 以88.6 mg的产率得到8-C-β-D-glucopyranosylorobol
  参考文献：
  名称：

  Total synthesis of two isoflavone C-glycosides: genistein and orobol 8-C-β-d-glucopyranosides

  摘要：

  Genistein and orobol 8-C-beta-D-glucopyranosides (1 and 3) were firstly synthesized in overall yields of 39% and 41% from 2,4-di-O-benzylphloroacetophenone (4), as follows: (1) the formation of the chalcone (6, 7) by aldol condensation of the benzyl-protected C-glycosylphloroacetophenone (5), a key intermediate of the total synthesis of I and 3 and synthesized by a C-glycosylation method involving the O -> C glycoside rearrangement of 4 in 96% yield; (2) the formation of isoflavones (10, 11 and 12, 13) by the formation of acetals by oxidative rearrangement of the protected chalcones (8 and 9) using TI(NO3)(3), followed by acid-catalyzed cyclization: (3) a final debenzylation by hydrogenolysis. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.03.038
• 作为产物：
  描述：

  3,4-二苄氧基苯甲醛 在 吡啶 、 4-二甲氨基吡啶 、 sodium methylate 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 40.0h， 生成 2'-acetoxy-3,4,4',6'-tetra(benzyloxy)-3'-C-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)chalcone
  参考文献：
  名称：

  Total synthesis of two isoflavone C-glycosides: genistein and orobol 8-C-β-d-glucopyranosides

  摘要：

  Genistein and orobol 8-C-beta-D-glucopyranosides (1 and 3) were firstly synthesized in overall yields of 39% and 41% from 2,4-di-O-benzylphloroacetophenone (4), as follows: (1) the formation of the chalcone (6, 7) by aldol condensation of the benzyl-protected C-glycosylphloroacetophenone (5), a key intermediate of the total synthesis of I and 3 and synthesized by a C-glycosylation method involving the O -> C glycoside rearrangement of 4 in 96% yield; (2) the formation of isoflavones (10, 11 and 12, 13) by the formation of acetals by oxidative rearrangement of the protected chalcones (8 and 9) using TI(NO3)(3), followed by acid-catalyzed cyclization: (3) a final debenzylation by hydrogenolysis. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.03.038