1,3-diacetoxy-5-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)benzene | 6743-86-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1,3-diacetoxy-5-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)benzene
• 英文别名: 1,3-diacetoxy-5-(tetra-O-acetyl-β-D-glucopyranosiloxy)-benzene；3,5-diacetoxyphenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside；(3,5-Diacetoxyphenyl)-tetraacetyl-β-D-glucosid；Phloroglucinol-β-D-glucosid-hexaacetat；[(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-(3,5-diacetyloxyphenoxy)oxan-2-yl]methyl acetate
• CAS: 6743-86-8
• 化学式: C₂₄H₂₈O₁₄
• 分子量: 540.478
• InChiKey: NPYZETSBCZCOAG-GNADVCDUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  38
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  176
• 氢给体数：
  0
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  phloroglucinol diacetate 、 2,3,4,6-四-O-乙酰基-α-D-吡喃葡萄糖酰氟 在 4 A molecular sieve 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 以37%的产率得到3,5-diacetoxyphenyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside
  参考文献：
  名称：

  通过O→CGlycoside重排实际合成aC-糖基黄酮

  摘要：

  2,3,4,6-四-O-苄基-α-D-吡喃葡萄糖基氟和2-乙酰间苯三酚3,5-双（烷基醚）在三氟化硼醚化物作为活化剂存在下的C-糖基化立体选择性地得到通过 O → C 糖苷重排，β-C-糖苷的产率很高。随后，C-葡萄糖苷与苯甲醛的羟醛缩合以良好的收率提供相应的β-C-葡萄糖基查耳酮。

  DOI：

  10.1246/bcsj.68.1379

文献信息

• Synthesis of 1-[3,5-bis-(2,3,4,6-tetra-O-acetyl-β-d-glucopyranosyl)-2,4,6-trihydroxyphenyl]ethanone: An intermediate of potential usefulness for synthesis of bis-C-glucosyl flavonoids
  作者：Toshihiro Kumazawa、Mitsuo Ishida、Shigeru Matsuba、Shingo Sato、Jun-ichi Onodera

  DOI：10.1016/s0008-6215(96)00280-7

  日期：1997.2

  Bis-glycosylation of 3,5-dibenzyloxyphenol with 2,3,4,6-tetra-O-benzyl-alpha-D-glucopyranosyl fluoride in a two-step sequence produced the bis-glucosylated product, 3,5-dibenzyloxy-2,6-bis-(2,3,4,6-tetra-O-benzyl-beta-D-glucopyranosyl)phenol. Subsequent hydrogenolytic debenzylation and acetylation gave the undeca-O-acetyl derivative, which, when subjected to a Friedel-Crafts acylation with borontrifluoride-acetic acid, gave the 4-C-acetyl target compound, 1-[3,5-bis-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)-2,4,6-trihydroxyphenyl]-ethanone. (C) 1997 Elsevier Science Ltd.
• Practical Synthesis of a<i>C</i>-Glycosyl Flavonoid via<i>O</i>→<i>C</i>Glycoside Rearrangement
  作者：Toshihiro Kumazawa、Kazuhito Ohki、Mitsuo Ishida、Shingo Sato、Jun-ichi Onodera、Shigeru Matsuba

  DOI：10.1246/bcsj.68.1379

  日期：1995.5

  The C-glycosylation of 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl fluoride and 2-acetylphloroglucinol 3,5-bis(alkyl ether) in the presence of boron trifluoride etherate as an activator stereoselectively gave the β-C-glucoside in a good yield via O → C glycoside rearrangement. Subsequently, aldol condensation of the C-glucoside with benzaldehyde afforded the corresponding β-C-glucosyl chalcone in a good

  2,3,4,6-四-O-苄基-α-D-吡喃葡萄糖基氟和2-乙酰间苯三酚3,5-双（烷基醚）在三氟化硼醚化物作为活化剂存在下的C-糖基化立体选择性地得到通过 O → C 糖苷重排，β-C-糖苷的产率很高。随后，C-葡萄糖苷与苯甲醛的羟醛缩合以良好的收率提供相应的β-C-葡萄糖基查耳酮。