(E)-1-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-4-(4-chlorophenyl)but-3-en-2-one | 1042966-22-2

• 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-(4-chlorophenyl)but-3-en-2-one
• 英文别名: [(2R,3R,4R,5S,6S)-3,4,5-triacetyloxy-6-[(E)-4-(4-chlorophenyl)-2-oxobut-3-enyl]oxan-2-yl]methyl acetate
• CAS: 1042966-22-2
• 化学式: C₂₄H₂₇ClO₁₀
• 分子量: 510.925
• InChiKey: NNCMKUGWLZAXOZ-CPPXKNBNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  35
• 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-(4-chlorophenyl)but-3-en-2-one 在 sodium tetrahydroborate 、 cerium(III) chloride hexahydrate 、 indium(III) chloride tetrahydrate 、 甲基磺酰氯 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 7.75h， 生成 1-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-4-(4-chlorophenyl)anthracene-9,10-(1H,4H)dione
  参考文献：
  名称：

  一个策略蒽醌类芳基-的合成Ç -glycosides

  摘要：

  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。

  DOI：

  10.1021/jo302589t
• 作为产物：
  描述：

  D-葡萄糖 在 四氢吡咯 、 吡啶 、 碳酸氢钠 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 72.0h， 生成 (E)-1-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-4-(4-chlorophenyl)but-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

• 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.
• 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.