(N-benzylcarbamoyl)methyl 3,6-di-O-acetyl-2,4-dideoxy-2-C-[(E)-(ethoxycarbonyl)methylene]-α-D-glycero-hex-3-enopyranoside

• 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: (N-benzylcarbamoyl)methyl 3,6-di-O-acetyl-2,4-dideoxy-2-C-[(E)-(ethoxycarbonyl)methylene]-α-D-glycero-hex-3-enopyranoside
• 英文别名: ethyl (2E)-2-[(2S,6S)-4-acetyloxy-2-(acetyloxymethyl)-6-[2-(benzylamino)-2-oxoethoxy]-2H-pyran-5-ylidene]acetate
• 化学式: C₂₃H₂₇NO₉
• 分子量: 461.469
• InChiKey: BKTLDSDZZFRKFI-YWMMNZTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  33
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  127
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  3,4,6-tri-O-acetyl carboxymethyl-α-D-glucopyranoside-2-O-lactone 在 乙酸酐 、 二甲基亚砜 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 34.0h， 生成 (N-benzylcarbamoyl)methyl 3,6-di-O-acetyl-2,4-dideoxy-2-C-[(E)-(ethoxycarbonyl)methylene]-α-D-glycero-hex-3-enopyranoside
  参考文献：
  名称：

  Synthesis of sugars embodying conjugated carbonyl systems and related triazole derivatives from carboxymethyl glycoside lactones. Evaluation of their antimicrobial activity and toxicity

  摘要：

  The synthesis of a series of pyranoid derivatives comprising a conjugated carbonyl function and related triazole derivatives, structurally suitable for bioactivity evaluation, was achieved in few steps starting from readily available carboxymethyl glycoside lactones (CMGL). 3-Enopyranosid-2-uloses were generated by oxidation/elimination of tri-O-acylated 2-hydroxy pyranosides. Subsequent Wittig olefination provided stereoselectively 2-C-branched-chain conjugated dienepyranosides with (E)-configuration around the exocyclic double bond. A heterogeneous CuI/Amberlyst-catalyzed 'click' chemistry protocol was used to convert glycosides bearing a propargyl moiety into the corresponding 1,2,3-triazoles. These new molecules were screened for their in vitro antibacterial and antifungal activities and those containing conjugated carbonyl systems demonstrated the best efficacy. (N-Dodecylcarbamoyl)methyl enone glycerosides were the most active ones among the enones tested. The alpha-anomer displayed very strong activities against Bacillus cereus and Bacillus subtilis and strong activity toward Enterococcus faecalis and the fungal pathogen Penicillium aurantiogriseum. The corresponding beta-anomer presented a very strong inhibitory effect against two fungal species (Aspergillus niger and P. aurantiogriseum). (N-Dodecyl-/N-propargyl/or N-benzylcarbamoyl) methyl dienepyranosides exhibited selectively a strong activity toward E. faecalis. Further acute toxicity evaluation indicated low toxic effect of the (N-dodecylcarbamoyl)methyl enone glyceroside alpha-anomer and of the carbamoylmethyl dienepyranosides N-protected with propargyl or benzyl groups. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.11.060

文献信息

• Synthesis of sugars embodying conjugated carbonyl systems and related triazole derivatives from carboxymethyl glycoside lactones. Evaluation of their antimicrobial activity and toxicity
  作者：Nuno M. Xavier、Margarida Goulart、Ana Neves、Jorge Justino、Stéphane Chambert、Amélia P. Rauter、Yves Queneau

  DOI：10.1016/j.bmc.2010.11.060

  日期：2011.1

  The synthesis of a series of pyranoid derivatives comprising a conjugated carbonyl function and related triazole derivatives, structurally suitable for bioactivity evaluation, was achieved in few steps starting from readily available carboxymethyl glycoside lactones (CMGL). 3-Enopyranosid-2-uloses were generated by oxidation/elimination of tri-O-acylated 2-hydroxy pyranosides. Subsequent Wittig olefination provided stereoselectively 2-C-branched-chain conjugated dienepyranosides with (E)-configuration around the exocyclic double bond. A heterogeneous CuI/Amberlyst-catalyzed 'click' chemistry protocol was used to convert glycosides bearing a propargyl moiety into the corresponding 1,2,3-triazoles. These new molecules were screened for their in vitro antibacterial and antifungal activities and those containing conjugated carbonyl systems demonstrated the best efficacy. (N-Dodecylcarbamoyl)methyl enone glycerosides were the most active ones among the enones tested. The alpha-anomer displayed very strong activities against Bacillus cereus and Bacillus subtilis and strong activity toward Enterococcus faecalis and the fungal pathogen Penicillium aurantiogriseum. The corresponding beta-anomer presented a very strong inhibitory effect against two fungal species (Aspergillus niger and P. aurantiogriseum). (N-Dodecyl-/N-propargyl/or N-benzylcarbamoyl) methyl dienepyranosides exhibited selectively a strong activity toward E. faecalis. Further acute toxicity evaluation indicated low toxic effect of the (N-dodecylcarbamoyl)methyl enone glyceroside alpha-anomer and of the carbamoylmethyl dienepyranosides N-protected with propargyl or benzyl groups. (C) 2010 Elsevier Ltd. All rights reserved.