4',8-dihydoxyisoflavon-7-yl 2,3,5-tri-O-benzoyl-α-D-arabinofuranoside | 229612-60-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: 4',8-dihydoxyisoflavon-7-yl 2,3,5-tri-O-benzoyl-α-D-arabinofuranoside
• 英文别名: [(2R,3R,4S,5R)-3,4-dibenzoyloxy-5-[8-hydroxy-3-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxyoxolan-2-yl]methyl benzoate
• CAS: 229612-60-6
• 化学式: C₄₁H₃₀O₁₂
• 分子量: 714.682
• InChiKey: DWOJIXGYKZERCH-SPHZVSKWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  53
• 可旋转键数：
  13
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  164
• 氢给体数：
  2
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  4',8-dihydoxyisoflavon-7-yl 2,3,5-tri-O-benzoyl-α-D-arabinofuranoside 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 16.0h， 以76%的产率得到4',8-dihydroxyisoflavone 7-O-α-D-arabinofuranoside
  参考文献：
  名称：

  Synthesis of 4′,8-dihydroxyisoflavon-7-yl α-d-arabinofuranoside

  摘要：

  4',8-Dihydroxyisoflavon-7-yl alpha-D-arabinofuranoside 1 (A-76202), which is a strong alpha-glucosidase I and II inhibitor, was synthesized by the glycosylation of 2,3,5-tri-O-benzyl-alpha-D-arabinofuranosyl bromide 2 and the lithium salt of 4',8-diallyloxy-7-hydroxyisoflavone 4, and successive deprotection of allyl groups and benzoyl esters of the glycosylated product 5. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00135-4
• 作为产物：
  描述：

  2,3,5-三-O-苯甲酰基-alpha-D-阿拉伯呋喃糖基溴化物 在 rhodium(III) chloride 、 正丁基锂 作用下， 以 乙醇 为溶剂， 反应 13.58h， 生成 4',8-dihydoxyisoflavon-7-yl 2,3,5-tri-O-benzoyl-α-D-arabinofuranoside
  参考文献：
  名称：

  Synthesis of 4′,8-dihydroxyisoflavon-7-yl α-d-arabinofuranoside

  摘要：

  4',8-Dihydroxyisoflavon-7-yl alpha-D-arabinofuranoside 1 (A-76202), which is a strong alpha-glucosidase I and II inhibitor, was synthesized by the glycosylation of 2,3,5-tri-O-benzyl-alpha-D-arabinofuranosyl bromide 2 and the lithium salt of 4',8-diallyloxy-7-hydroxyisoflavone 4, and successive deprotection of allyl groups and benzoyl esters of the glycosylated product 5. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00135-4

文献信息

• Synthesis of 4′,8-dihydroxyisoflavon-7-yl α-d-arabinofuranoside
  作者：Masao Shiozaki

  DOI：10.1016/s0957-4166(99)00135-4

  日期：1999.4

  4',8-Dihydroxyisoflavon-7-yl alpha-D-arabinofuranoside 1 (A-76202), which is a strong alpha-glucosidase I and II inhibitor, was synthesized by the glycosylation of 2,3,5-tri-O-benzyl-alpha-D-arabinofuranosyl bromide 2 and the lithium salt of 4',8-diallyloxy-7-hydroxyisoflavone 4, and successive deprotection of allyl groups and benzoyl esters of the glycosylated product 5. (C) 1999 Elsevier Science Ltd. All rights reserved.