5,4'-di-O-hexanoylapigenin-7-O-2,3,4,6-tetra-O-benzoyl-β-D-glucopyranoside | 1145669-48-2

• 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: 5,4'-di-O-hexanoylapigenin-7-O-2,3,4,6-tetra-O-benzoyl-β-D-glucopyranoside
• 英文别名: 5,4'-di-O-hexanoylapigenin-7-yl-2,3,4,6-tetra-O-benzoyl-β-D-glucopyranoside；[(2R,3R,4S,5R,6S)-3,4,5-tribenzoyloxy-6-[5-hexanoyloxy-2-(4-hexanoyloxyphenyl)-4-oxochromen-7-yl]oxyoxan-2-yl]methyl benzoate
• CAS: 1145669-48-2
• 化学式: C₆₁H₅₆O₁₆
• 分子量: 1045.11
• InChiKey: BXBKWGHMEKRHJR-LMLCQYFMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.7
• 重原子数：
  77
• 可旋转键数：
  28
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  203
• 氢给体数：
  0
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  5,4'-di-O-hexanoylapigenin-7-O-2,3,4,6-tetra-O-benzoyl-β-D-glucopyranoside 在 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 以77%的产率得到芹甙元-7-葡萄糖苷
  参考文献：
  名称：

  Highly regioselective dehexanoylation in fully hexanoylated flavonoids

  摘要：

  Highly selective removal of the 7-O-hexanoyl group in fully hexanoylated flavones, isoflavones, flavanone, and flavonol was achieved under mild conditions using K2CO3 in a 1:1 mixture of CH3OH-CH2Cl2. The resulting 7-OH flavonoids are valuable intermediates for the synthesis of flavonoid 7-O-glycosides via phase-transfer-catalyzed (PTC) glycosylation. (C) 2018 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2018.11.015
• 作为产物：
  描述：

  德国春黄菊油 在 4-二甲氨基吡啶 、 四丁基溴化铵 、 potassium carbonate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 氯仿 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 28.5h， 生成 5,4'-di-O-hexanoylapigenin-7-O-2,3,4,6-tetra-O-benzoyl-β-D-glucopyranoside
  参考文献：
  名称：

  Highly regioselective dehexanoylation in fully hexanoylated flavonoids

  摘要：

  Highly selective removal of the 7-O-hexanoyl group in fully hexanoylated flavones, isoflavones, flavanone, and flavonol was achieved under mild conditions using K2CO3 in a 1:1 mixture of CH3OH-CH2Cl2. The resulting 7-OH flavonoids are valuable intermediates for the synthesis of flavonoid 7-O-glycosides via phase-transfer-catalyzed (PTC) glycosylation. (C) 2018 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2018.11.015

文献信息

• The first total synthesis of 7-O-β-d-glucopyranosyl-4′-O-α-l-rhamnopyranosyl apigenin via a hexanoyl ester-based protection strategy
  作者：Qi Gao、Gaoyan Lian、Feng Lin

  DOI：10.1016/j.carres.2008.12.016

  日期：2009.3

  The first total synthesis of 7-O-beta-D-glucopyranosyl-4 '-O-alpha-L-rhamnopyranosyI apigenin 1, which exhibits good anti-hepatitis B virus and anti-stroke activities, was accomplished in six steps and 20% overall yield from apigenin. Another synthetic route, in which the target was obtained in seven steps, was also developed to prove the utility of a hexanoyl ester-based orthogonal protection strategy. The hexanoyl protection strategy provided all the flavonoid intermediates with good solubility and reactivity, enabled efficient selective protection and glycosylation, and provided a practical and effective synthetic strategy for flavonoids, starting from commercially available flavone. (C) 2008 Elsevier Ltd. All rights reserved.
• Highly regioselective dehexanoylation in fully hexanoylated flavonoids
  作者：Zhiwei Zheng、Ziyi Han、Li Cai、Dandan Zhou、Bryson R. Chavis、Changsheng Li、Qiang Sui、Kaiyuan Jiang、Qi Gao

  DOI：10.1016/j.tetlet.2018.11.015

  日期：2018.12

  Highly selective removal of the 7-O-hexanoyl group in fully hexanoylated flavones, isoflavones, flavanone, and flavonol was achieved under mild conditions using K2CO3 in a 1:1 mixture of CH3OH-CH2Cl2. The resulting 7-OH flavonoids are valuable intermediates for the synthesis of flavonoid 7-O-glycosides via phase-transfer-catalyzed (PTC) glycosylation. (C) 2018 Elsevier Ltd. All rights reserved.