(+)-endo-fenacholyl 4,6-di-O-acetyl-2,3-dideoxy-β-D-erythrohex-2-enopyranoside | 1432744-64-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (+)-endo-fenacholyl 4,6-di-O-acetyl-2,3-dideoxy-β-D-erythrohex-2-enopyranoside
• 英文别名: (+)-endo-fenacholyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside；[(2R,3S,6S)-3-acetyloxy-6-[[(1S,2S,4R)-1,3,3-trimethyl-2-bicyclo[2.2.1]heptanyl]oxy]-3,6-dihydro-2H-pyran-2-yl]methyl acetate
• CAS: 1432744-64-3
• 化学式: C₂₀H₃₀O₆
• 分子量: 366.455
• InChiKey: ASBXSFGNFJVMRX-ATZJQYBUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (+)-endo-fenacholyl 4,6-di-O-acetyl-2,3-dideoxy-β-D-erythrohex-2-enopyranoside 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 生成
  参考文献：
  名称：

  Synthesis and antibacterial properties of 2,3-dideoxyglucosides of terpene alcohols and phenols

  摘要：

  Essential oils and their oxygenated terpene constituents possess potent antimicrobial properties. In the present study, a facile synthetic route to the 2,3-dideoxy 1-O-glucosides of important phenols and terpene alcohols in excellent yields (85-96%) has been delineated. Studies on their antimicrobial action against four food-borne pathogens--Bacillus cereus, Staphylococcus aureus, Escherichia coli and Yersinia enterocolitica--demonstrated that the zone of inhibition, in general, was higher for the 2,3-unsaturated 1-O-glucoside derivatives (1b-6b) and the corresponding saturated glucosides (1c-5c) when compared to the parent alcohols/phenols (1-6). The minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC) values for these derivatives too were generally lower than those of the parent compounds. Furthermore, the time-kill and bacteriolysis assays too demonstrated the greater antimicrobial potential of the derivatives. The 2,3-dideoxy 1-O-glucosides of phenols and terpene alcohols were more effective in their antimicrobial action than the corresponding parent compounds. The study indicated that these novel derivatives can find useful application in control of food-related pathogenic microbes in foods.

  DOI：

  10.1016/j.foodchem.2015.03.078
• 作为产物：
  描述：

  溶剂红172 、 乙酰化葡萄烯糖 在 aluminum oxide 、 zinc(II) chloride 作用下， 反应 0.25h， 以84%的产率得到(+)-endo-fenacholyl 4,6-di-O-acetyl-2,3-dideoxy-β-D-erythrohex-2-enopyranoside
  参考文献：
  名称：

  ZnCl2/alumina impregnation catalyzed Ferrier rearrangement: an expedient synthesis of pseudoglycosides

  摘要：

  An improved method for the synthesis of 2,3-unsaturated-O-glycosides has been developed. ZnCl2 impregnated on activated alumina acts as an excellent reagent system for the conversion of 2,4,6-tri-O-acetyl-D-glucal to 2,3-unsaturated-O-glycosides with high alpha-selectivity. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.04.099

文献信息

• Y(OTf)3 as a highly efficient catalyst in Ferrier Rearrangement for the synthesis of O- and S-2,3-unsaturated glycopyranosides
  作者：Peiran Chen、Shan Li

  DOI：10.1016/j.tetlet.2014.08.092

  日期：2014.10

  By using Y(OTf)(3) as the catalyst, a series of 2,3-unsaturated-glucosides have been synthesized from 3,4,6-tri-O-acetyl-D-glucal, 3,4-di-O-acetyl-L-rhamnal, and 3,4,6-tri-O-benzyl-D-glucal under mild reaction conditions in good yields with high anomeric selectivities. It was found that, in this reaction, 3,4,6-tri-O-benzyl-D-glucal behaved differently from the other two glucals when it was reacted with phenol, O-benzyl glucoside instead of O-phenyl glucoside formed as the sole product. An explanation is given for this phenomenon. (C) 2014 Elsevier Ltd. All rights reserved.