(E)-1-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-4-(2-naphthyl)but-3-en-2-one | 1042966-23-3

• 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-(2-naphthyl)but-3-en-2-one
• 英文别名: (E)-1-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-4-(2-naphtyl)but-3-en-2-one；[(2R,3R,4R,5S,6S)-3,4,5-triacetyloxy-6-[(E)-4-naphthalen-2-yl-2-oxobut-3-enyl]oxan-2-yl]methyl acetate
• CAS: 1042966-23-3
• 化学式: C₂₈H₃₀O₁₀
• 分子量: 526.54
• InChiKey: BTIXXSXPKPEQKC-NNKNHSOJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  38
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 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-(2-naphthyl)but-3-en-2-one 在 sodium tetrahydroborate 、 cerium(III) chloride hexahydrate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以89%的产率得到(E)-1-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-2(R/S)-hydroxy-4-(2-naphathalenyl)but-3-ene
  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：

  2-萘甲醛 、 1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)propane-2-one 生成 (E)-1-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-4-(2-naphthyl)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

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.