2-(3,4-bisbenzyloxyphenyl)-5-hydroxy-7-(2-methylbenzyloxy)-6-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-4H-1-benzopyran-4-one | 321133-86-2

• 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: 2-(3,4-bisbenzyloxyphenyl)-5-hydroxy-7-(2-methylbenzyloxy)-6-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-4H-1-benzopyran-4-one
• 英文别名: 2-[3,4-bis(phenylmethoxy)phenyl]-5-hydroxy-7-[(2-methylphenyl)methoxy]-6-[(2S,3S,4R,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]chromen-4-one
• CAS: 321133-86-2
• 化学式: C₇₁H₆₄O₁₁
• 分子量: 1093.28
• InChiKey: GPKYHAWHDMHCGW-UIQIFNBJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.2
• 重原子数：
  82
• 可旋转键数：
  24
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  120
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  2-(3,4-bisbenzyloxyphenyl)-5-hydroxy-7-(2-methylbenzyloxy)-6-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-4H-1-benzopyran-4-one 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 反应 4.5h， 以100%的产率得到异荭草素
  参考文献：
  名称：

  An effective synthesis of isoorientin: the regioselective synthesis of a 6-C-glucosylflavone

  摘要：

  Isoorientin, a 6-C-beta -D-glucopyranosyl-3',4',5,7-tetrahydroxyflavone, was synthesized in a 15% overall yield, in ten steps, starting from the commercially available phloroacetophenone. The C-glucosyl phloroacetophenone derivative, a synthetic intermediate that contains a free hydroxyl group that is para to the glucosyl moiety, was obtained by hydrogenolysis by taking advantage of differences in the hydrogenolysis rates between a benzyl protecting group and a 2-methylbenzyl protecting group. Aldol condensation of the C-glucosyl phloroacetophenone derivative with 3,4-bis-benzyloxybenzaldehyde afforded the corresponding chalcone as a precursor of the 6-C-glucosyl flavone. Construction of the flavone system by application of I-2-DMSO, followed by deprotection, yielded isoorientin. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(00)00226-3
• 作为产物：
  描述：

  3,4-二苄氧基苯甲醛 在 sodium hydroxide 、 碘 作用下， 以 1,4-二氧六环 、 水 、 二甲基亚砜 为溶剂， 反应 24.25h， 生成 2-(3,4-bisbenzyloxyphenyl)-5-hydroxy-7-(2-methylbenzyloxy)-6-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-4H-1-benzopyran-4-one
  参考文献：
  名称：

  An effective synthesis of isoorientin: the regioselective synthesis of a 6-C-glucosylflavone

  摘要：

  Isoorientin, a 6-C-beta -D-glucopyranosyl-3',4',5,7-tetrahydroxyflavone, was synthesized in a 15% overall yield, in ten steps, starting from the commercially available phloroacetophenone. The C-glucosyl phloroacetophenone derivative, a synthetic intermediate that contains a free hydroxyl group that is para to the glucosyl moiety, was obtained by hydrogenolysis by taking advantage of differences in the hydrogenolysis rates between a benzyl protecting group and a 2-methylbenzyl protecting group. Aldol condensation of the C-glucosyl phloroacetophenone derivative with 3,4-bis-benzyloxybenzaldehyde afforded the corresponding chalcone as a precursor of the 6-C-glucosyl flavone. Construction of the flavone system by application of I-2-DMSO, followed by deprotection, yielded isoorientin. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(00)00226-3

文献信息

• An effective synthesis of isoorientin: the regioselective synthesis of a 6-C-glucosylflavone
  作者：Toshihiro Kumazawa、Tomomi Minatogawa、Shigeru Matsuba、Shingo Sato、Jun-ichi Onodera

  DOI：10.1016/s0008-6215(00)00226-3

  日期：2000.11

  Isoorientin, a 6-C-beta -D-glucopyranosyl-3',4',5,7-tetrahydroxyflavone, was synthesized in a 15% overall yield, in ten steps, starting from the commercially available phloroacetophenone. The C-glucosyl phloroacetophenone derivative, a synthetic intermediate that contains a free hydroxyl group that is para to the glucosyl moiety, was obtained by hydrogenolysis by taking advantage of differences in the hydrogenolysis rates between a benzyl protecting group and a 2-methylbenzyl protecting group. Aldol condensation of the C-glucosyl phloroacetophenone derivative with 3,4-bis-benzyloxybenzaldehyde afforded the corresponding chalcone as a precursor of the 6-C-glucosyl flavone. Construction of the flavone system by application of I-2-DMSO, followed by deprotection, yielded isoorientin. (C) 2000 Elsevier Science Ltd. All rights reserved.