7-O-(2,3,4,6-tetra-O-acetyl-β-L-glucopyranosyl)-4'-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)apigenin | 679398-73-3

• 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: 7-O-(2,3,4,6-tetra-O-acetyl-β-L-glucopyranosyl)-4'-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)apigenin
• CAS: 679398-73-3
• 化学式: C₄₃H₄₆O₂₃
• 分子量: 930.824
• InChiKey: XSVRURCSSNBCAM-FGYWXYLISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.09
• 重原子数：
  66.0
• 可旋转键数：
  15.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  297.76
• 氢给体数：
  1.0
• 氢受体数：
  23.0

反应信息

• 作为反应物：
  描述：

  7-O-(2,3,4,6-tetra-O-acetyl-β-L-glucopyranosyl)-4'-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)apigenin 在 sodium methylate 作用下， 以 甲醇 、 氯仿 为溶剂， 以94%的产率得到apigenin 7-O-β-L-glucoside-4'-O-β-D-glucoside
  参考文献：
  名称：

  Chiral Molecular Recognition on Formation of a Metalloanthocyanin: A Supramolecular Metal Complex Pigment from Blue Flowers ofSalvia patens

  摘要：

  The chirality of the sugar moiety is responsible for the chiral molecular recognition on formation of a metalloanthocyanin from Salvia patens. This mechanism was revealed by using the synthetic apigenin 7,4'-diglucosides derived from D- or L-glucose. The supermolecule consists of six malonylawobanin molecules (blue) coordinated to two Mg2+ ions (red) with an M-helical arrangement of six 7,4'-diglucoside molecules (yellow) intercalated.

  DOI：

  10.1002/1521-3773(20010302)40:5<894::aid-anie894>3.0.co;2-8
• 作为产物：
  描述：

  2,3,4,6-tetra-O-acetyl-α-L-glucopyranosyl bromide 在 喹啉 、 2,6-二叔丁基-4-甲基吡啶 、 三氟化硼乙醚 、 silver carbonate 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 四甲基胍 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 氯苯 为溶剂， 反应 19.0h， 生成 7-O-(2,3,4,6-tetra-O-acetyl-β-L-glucopyranosyl)-4'-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)apigenin
  参考文献：
  名称：

  Total synthesis of apigenin 7,4′-di-O-β-glucopyranoside, a component of blue flower pigment of Salvia patens, and seven chiral analogues

  摘要：

  We have succeeded in the first total synthesis of apigenin 7,4'-di-O-beta-D-glucopyranoside (1a), a component of blue pigment, protodelphin, from naringenin (2). Glycosylation of 2 according to Koenigs-Knorr reaction provided a monoglucoside 4a in 80% yield, and this was followed by DDQ oxidation to give apigenin 7-O-glucoside (12a). Further glycosylation of 4'-OH of 12a with 2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl fluoride (5a) was achieved using a Lewis acid-and-base promotion system (BF3.Et2O, 2,6-di-tert-butyl-4-methylpyridine, and 1,1,3,3-tetramethylguanidine) in 70% yield, and subsequent deprotection produced 1a. Synthesis of three other chiral isomers of 1a, with replacement Of D-glucose at 7 and/or 4'-OH by L-glucose (1b-d), and four chiral isomers of apigenin 7-O-beta-glucosides (6a,b) and 4'-O-beta-glucosides (7a,b) also proved possible. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.01.001