(Z)-4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)but-2-enenitrile | 333748-90-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (Z)-4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)but-2-enenitrile
• 英文别名: 2,3,4,6-Tetra-O-acetylalliarinoside；[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[(Z)-3-cyanoprop-2-enoxy]oxan-2-yl]methyl acetate
• CAS: 333748-90-6
• 化学式: C₁₈H₂₃NO₁₀
• 分子量: 413.381
• InChiKey: IZTCRAZMRMVXSX-ILFVIUNKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  29
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  147
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (Z)-4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)but-2-enenitrile 在 三氟甲磺酸 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以85%的产率得到alliarinoside
  参考文献：
  名称：

  Synthesis of the allelochemical alliarinoside present in garlic mustard (Alliaria petiolata), an invasive plant species in North America

  摘要：

  The allelochemical alliarinoside present in garlic mustard (Alliaria petiolata), an invasive plant species in North America, was chemically synthesized using an efficient and practical synthetic strategy based on a simple reaction sequence. Commercially available 1,2,3,4,6-penta-O-acetyl-beta-D-glucopyranose was converted into prop-2-enyl 2',3',4',6'-tetra-O-acetyl-beta-D-glucopyranoside and subjected to epoxidation. In a one-pot reaction, ring-opening of the epoxide using TMSCN under solvent free conditions followed by treatment of the formed trimethylsilyloxy nitrile with pyridine and phosphoryl chloride, afforded the acetylated beta-unsaturated nitriles (Z)-4-(2',3',4',6'-tetra-O-beta-D-glucopyranosyloxy)but-2-enenitrile and its isomer (E)-4-(2',3',4',6'-tetra-O-beta-D-glucopyranosyloxy)but-2-enenitrile. Deacetylation of Z-and/or E-isomers afforded the target molecules alliarinoside and its isomer. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2014.05.006
• 作为产物：
  描述：

  Acetic acid (2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-allyloxy-tetrahydro-pyran-4-yl ester 在 臭氧 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 (Z)-4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)but-2-enenitrile
  参考文献：
  名称：

  A Cyanoallyl Glucoside from Alliaria petiolata, as a Feeding Deterrent for Larvae of Pieris napi oleracea

  摘要：

  Alliarinoside, a feeding inhibitor against early instar larvae of Pieris napi oleracea, was isolated from the foliage of Alliaria petiolata and characterized as (2Z)-4-(beta -D-glucopyranosyloxy)-2-butenenitrile (1) by spectroscopic methods. The structural assignment was confirmed by synthesis of peracetylated alliarinoside (2) and its 2E isomer (3). A sample of synthetic 1 was isolated by preparative HPLC from the hydrolysis of the 2Z acetate. Feeding inhibition assays showed comparable activity for the synthetic and natural glycosides.

  DOI：

  10.1021/np000534d

文献信息

• Copper-catalyzed Cyanation of Alkenyl Iodides
  作者：Sidney Wilkerson-Hill

  DOI：10.15227/orgsyn.093.0163

  日期：——

  Acetone cyanohydrin is highly toxic and must be handled in a well-ventilated fume hood. The aqueous waste solutions should not be in contact with acids and, where permitted, must be treated with excess commercial Clorox (R) bleach. All glassware and apparatus that comes into contact with it must be washed with commercial Clorox (R) bleach. All spills around balances or work areas should be immediately cleaned up and the area washed down with bleach.