5-benzoyl-4'-benzyloxy-6-C-(2'',3'',4'',6''-tetra-O-benzyl-β-D-glucopyranosyl)-7-methoxyflavone | 1437307-71-5

• 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: 5-benzoyl-4'-benzyloxy-6-C-(2'',3'',4'',6''-tetra-O-benzyl-β-D-glucopyranosyl)-7-methoxyflavone
• 英文别名: [7-methoxy-4-oxo-2-(4-phenylmethoxyphenyl)-6-[(2S,3S,4R,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]chromen-5-yl] benzoate
• CAS: 1437307-71-5
• 化学式: C₆₄H₅₆O₁₁
• 分子量: 1001.14
• InChiKey: GMQAAGNXTKMTLC-LXVQLMPCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.1
• 重原子数：
  75
• 可旋转键数：
  22
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  117
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  5-benzoyl-4'-benzyloxy-6-C-(2'',3'',4'',6''-tetra-O-benzyl-β-D-glucopyranosyl)-7-methoxyflavone 在 吡啶 、 palladium 10% on activated carbon 、 氢气 、 silver carbonate 、 四甲基胍 作用下， 以 喹啉 、 乙醇 、 乙酸乙酯 、 乙腈 为溶剂， 反应 12.0h， 生成 5-benzoyl-6-C-(2'',3'',4'',6''-tetra-O-acetyl-β-D-glucopyranosyl)-4'-O-(2''',3''',4''',6'''-tetra-O-acetyl-β-D-glucopyranosyl)-7-methoxyflavone
  参考文献：
  名称：

  Concise synthesis of flavocommelin, 7-O-methylapigenin 6-C-, 4′-O-bis-β-d-glucoside, a component of the blue supramolecular pigment from Commelina communis

  摘要：

  Flavocommelin, 7-O-methylapigenin 6-C-, 4 '-O-bis-beta-D-glucoside, was synthesized in 9 steps from the C-glycosylation of 6-O-benzy-4-O-methylphloroacetophenone via the introduction of a cinnamoyl residue by aldol condensation and the formation of a C-ring by regioselective and oxidative ring-closure to regio-and stereoselective O-glycosylation for an overall yield of 31%. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2013.03.016
• 作为产物：
  描述：

  2,3,4,6-四-O-苯基-Alpha-D-吡喃葡萄糖基三氯乙酰亚氨酸 在 吡啶 、 三氟甲磺酸三甲基硅酯 、 三氟化硼乙醚 、 sodium methoxide 、 碘 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 0.5h， 生成 5-benzoyl-4'-benzyloxy-6-C-(2'',3'',4'',6''-tetra-O-benzyl-β-D-glucopyranosyl)-7-methoxyflavone
  参考文献：
  名称：

  Concise synthesis of flavocommelin, 7-O-methylapigenin 6-C-, 4′-O-bis-β-d-glucoside, a component of the blue supramolecular pigment from Commelina communis

  摘要：

  Flavocommelin, 7-O-methylapigenin 6-C-, 4 '-O-bis-beta-D-glucoside, was synthesized in 9 steps from the C-glycosylation of 6-O-benzy-4-O-methylphloroacetophenone via the introduction of a cinnamoyl residue by aldol condensation and the formation of a C-ring by regioselective and oxidative ring-closure to regio-and stereoselective O-glycosylation for an overall yield of 31%. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2013.03.016

文献信息

• Concise synthesis of flavocommelin, 7-O-methylapigenin 6-C-, 4′-O-bis-β-d-glucoside, a component of the blue supramolecular pigment from Commelina communis
  作者：Kazufumi Misawa、Yoshiki Gunji、Shingo Sato

  DOI：10.1016/j.carres.2013.03.016

  日期：2013.6

  Flavocommelin, 7-O-methylapigenin 6-C-, 4 '-O-bis-beta-D-glucoside, was synthesized in 9 steps from the C-glycosylation of 6-O-benzy-4-O-methylphloroacetophenone via the introduction of a cinnamoyl residue by aldol condensation and the formation of a C-ring by regioselective and oxidative ring-closure to regio-and stereoselective O-glycosylation for an overall yield of 31%. (C) 2013 Elsevier Ltd. All rights reserved.