(E)-1-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-4-phenylbut-3-en-2-one | 1042966-18-6

• 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',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-4-phenylbut-3-en-2-one
• 英文别名: [(2R,3R,4R,5S,6S)-3,4,5-triacetyloxy-6-[(E)-2-oxo-4-phenylbut-3-enyl]oxan-2-yl]methyl acetate
• CAS: 1042966-18-6
• 化学式: C₂₄H₂₈O₁₀
• 分子量: 476.48
• InChiKey: OWQKUTQPFIFHIJ-SEZSGAEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  34
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  132
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (E)-1-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-4-phenylbut-3-en-2-one 在 甲醇 、 sodium methylate 作用下， 以65%的产率得到(E)-1-(β-D-glucopyranosyl)-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：

  1-(β-D-glucopyranosyl)propan-2-one 在 四氢吡咯 、 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 生成 (E)-1-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-4-phenylbut-3-en-2-one
  参考文献：
  名称：

  Synthesis of C -glycosylmethyl isoxazoles via aerobic oxidation of ketoximes catalyzed by TEMPO

  摘要：

  An efficient and high yielding synthesis of C-glycosylmethyl isoxazoles by oxidation of ketoximes in the presence of oxygen and mediated by TEMPO is described. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2017.03.005

文献信息

• A Strategy for the Synthesis of Anthraquinone-Based Aryl-<i>C</i>-glycosides
  作者：Namrata Anand、Kapil Upadhyaya、Arya Ajay、Rohit Mahar、Sanjeev K. Shukla、Brijesh Kumar、Rama Pati Tripathi

  DOI：10.1021/jo302589t

  日期：2013.5.17

  efficient and simple strategy for the synthesis of a diverse range of anthraquinone-based aryl-C-glycosides has been developed. It involves the sequential Diels–Alder reaction and oxidative aromatization with the preformed glycosyl diene and dienophiles. The glycosyl dienes were obtained from simple sugars by tandem one-pot substitution and elimination reaction.

  对于不同范围的蒽醌基芳基的合成的有效和简单的策略Ç -glycosides已经研制成功。它涉及顺序的Diels-Alder反应以及预先形成的糖基二烯和亲二烯体的氧化芳构化作用。通过串联一锅取代和消除反应从单糖获得糖基二烯。
• Aldol reaction of β-C-glycosylic ketones: synthesis of C-(E)-cinnamoyl glycosylic compounds as precursors for new biologically active C-glycosides
  作者：Surendra Singh Bisht、Jyoti Pandey、Anindra Sharma、Rama Pati Tripathi

  DOI：10.1016/j.carres.2008.04.021

  日期：2008.7

  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.
• Synthesis of C -glycosylmethyl isoxazoles via aerobic oxidation of ketoximes catalyzed by TEMPO
  作者：Helberth Llantén、Sebastian Barata-Vallejo、Al Postigo、Pedro A. Colinas

  DOI：10.1016/j.tetlet.2017.03.005

  日期：2017.4

  An efficient and high yielding synthesis of C-glycosylmethyl isoxazoles by oxidation of ketoximes in the presence of oxygen and mediated by TEMPO is described. (C) 2017 Elsevier Ltd. All rights reserved.
• Synthetic studies in butenonyl C-glycosides: Preparation of polyfunctional alkanonyl glycosides and their enzyme inhibitory activity
  作者：Surendra Singh Bisht、Seerat Fatima、Akhilesh K. Tamrakar、Neha Rahuja、Natasha Jaiswal、Arvind K. Srivastava、Rama P. Tripathi

  DOI：10.1016/j.bmcl.2009.03.136

  日期：2009.5

  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.