(E)-1-(2',3',4'-tri-O-acetyl-β-D-xylopyranosyl)-4-(4'-chlorophenyl)but-3-en-2-one | 1164131-67-2

• 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: (E)-1-(2',3',4'-tri-O-acetyl-β-D-xylopyranosyl)-4-(4'-chlorophenyl)but-3-en-2-one
• CAS: 1164131-67-2
• 化学式: C₂₁H₂₃ClO₈
• 分子量: 438.862
• InChiKey: XFRJRLJUIPTXRD-RKCKKFMASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.51
• 重原子数：
  30.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  105.2
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (E)-1-(2',3',4'-tri-O-acetyl-β-D-xylopyranosyl)-4-(4'-chlorophenyl)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96%的产率得到(E)-1-(2',3',4'-tri-O-acetyl-β-D-xylopyranosyl)-2(R/S)-hydroxy-4-(4-chlorophenyl)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

文献信息

• 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.