(N-dodecylcarbamoyl)methyl 3,6-di-O-acetyl-4-deoxy-α-D-glycero-hex-3-enopyranosid-2-ulose | 1269664-05-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: (N-dodecylcarbamoyl)methyl 3,6-di-O-acetyl-4-deoxy-α-D-glycero-hex-3-enopyranosid-2-ulose
• 英文别名: [(2S,6S)-4-acetyloxy-6-[2-(dodecylamino)-2-oxoethoxy]-5-oxo-2H-pyran-2-yl]methyl acetate
• CAS: 1269664-05-2
• 化学式: C₂₄H₃₉NO₈
• 分子量: 469.576
• InChiKey: YVNIQRDDTGRYOX-RDPSFJRHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  33
• 可旋转键数：
  19
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  117
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (N-dodecylcarbamoyl)methyl 3,6-di-O-acetyl-4-deoxy-α-D-glycero-hex-3-enopyranosid-2-ulose 、 乙氧甲酰基亚甲基三苯基膦 以 氯仿 为溶剂， 反应 1.0h， 以54%的产率得到(N-dodecylcarbamoyl)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
• 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 为溶剂， 反应 32.0h， 生成 (N-dodecylcarbamoyl)methyl 3,6-di-O-acetyl-4-deoxy-α-D-glycero-hex-3-enopyranosid-2-ulose
  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