6-benzyloxy-2-hydroxy-4-(2-methylbenzyloxy)-3-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)acetophenone | 321133-82-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-benzyloxy-2-hydroxy-4-(2-methylbenzyloxy)-3-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)acetophenone
• 英文别名: 1-[2-hydroxy-4-[(2-methylphenyl)methoxy]-6-phenylmethoxy-3-[(2S,3S,4R,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]phenyl]ethanone
• CAS: 321133-82-8
• 化学式: C₅₇H₅₆O₉
• 分子量: 885.066
• InChiKey: VYFYXNPQVYGYCS-QGGCDQADSA-N

物化性质

• 沸点：
  922.3±65.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  10.2
• 重原子数：
  66
• 可旋转键数：
  21
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  6-benzyloxy-2-hydroxy-4-(2-methylbenzyloxy)-3-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)acetophenone 在 palladium on activated charcoal sodium hydroxide 、 氢气 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 29.0h， 生成 3,4-dibenzyloxy-6'-hydroxy-2',4'-bis(2-methylbenzyloxy)-3'-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)chalcone
  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：

  1-(2-(benzyloxy)-4,6-dihydroxyphenyl)ethan-1-one 在 4 A molecular sieve 、 三氟化硼乙醚 、 potassium carbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 6-benzyloxy-2-hydroxy-4-(2-methylbenzyloxy)-3-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)acetophenone
  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.