(E)-1-(2',3',6',2'',3'',4'',6''-hepta-O-acetyl-β-cellobiosyl)-4-phenylbut-3-en-2-one | 1042966-29-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-1-(2',3',6',2'',3'',4'',6''-hepta-O-acetyl-β-cellobiosyl)-4-phenylbut-3-en-2-one
• 英文别名: (E)-1-(2',3',6',2'',3'',4'',5''-hepta-O-acetyl-β-cellobiosyl)-4-phenylbut-3-en-2-one；[(2R,3R,4S,5S,6S)-4,5-diacetyloxy-6-[(E)-2-oxo-4-phenylbut-3-enyl]-3-[(2S,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl acetate
• CAS: 1042966-29-9
• 化学式: C₃₆H₄₄O₁₈
• 分子量: 764.735
• InChiKey: FQQBVZQIGUOSBL-BWRHMAAYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  54
• 可旋转键数：
  22
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  229
• 氢给体数：
  0
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  (E)-1-(2',3',6',2'',3'',4'',6''-hepta-O-acetyl-β-cellobiosyl)-4-phenylbut-3-en-2-one 在 甲醇 、 sodium methylate 作用下， 以65%的产率得到(E)-1-(β-cellobiosyl)-4-phenyl-but-3-en-2-one
  参考文献：
  名称：

  Synthetic studies in butenonyl C-glycosides: Preparation of polyfunctional alkanonyl glycosides and their enzyme inhibitory activity

  摘要：

  A simple synthesis of phenyl butenoyl C-glycosides has been achieved by Aldol condensation of peracetylated glycosyl acetones with aromatic aldehydes followed by deacetylation with methanolic NaOMe. The selected butenoyl C-glycosides on conjugate addition of diethyl malonate resulted in polyfunctional alkanonyl glycosides in good yields. The butenoyl C- and alkanoyl C- glycosides were evaluated for their alpha-glucosidase, glucose-6-phosphatse and glycogen phosphorylase enzyme inhibitory activities in vitro. Three of the synthesized (3, 5 and 9) showed potent enzyme inhibitory activities as compared to standard drugs. Compounds 3, 5 and 9 were evaluated in vivo too displaying significant activity as compared to standard drugs acarbose and metformin. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.03.136
• 作为产物：
  描述：

  苯甲醛 、 1-(2',3',6',2'',3'',4'',6''-hepta-O-acetyl-β-cellobiosyl)propan-2-one 在 四氢吡咯 作用下， 以 二氯甲烷 为溶剂， 反应 10.0h， 以71%的产率得到(E)-1-(2',3',6',2'',3'',4'',6''-hepta-O-acetyl-β-cellobiosyl)-4-phenylbut-3-en-2-one
  参考文献：
  名称：

  Aldol reaction of β-C-glycosylic ketones: synthesis of C-(E)-cinnamoyl glycosylic compounds as precursors for new biologically active C-glycosides

  摘要：

  A series of beta-C-glycosylic ketones were prepared starting from D-glucose, D-xylose, D-mannose, and cellobiose. The beta-C-glycosylic ketones on aldol condensation with different aromatic aldehydes in the presence of a suitable organocatalyst led to the formation of respective C-(E)-cinnamoyl glycosides stereoselectively in good yields as precursors for the synthesis of biologically active compounds. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.04.021