(N-propargylcarbamoyl)methyl 3,4,6-tri-O-acetyl-β-D-glucopyranoside | 1269663-98-0

• 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-propargylcarbamoyl)methyl 3,4,6-tri-O-acetyl-β-D-glucopyranoside
• CAS: 1269663-98-0
• 化学式: C₁₇H₂₃NO₁₀
• 分子量: 401.37
• InChiKey: GCEOCZNUOLZEIY-LMHBHQSJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.74
• 重原子数：
  28.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  146.69
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  (N-propargylcarbamoyl)methyl 3,4,6-tri-O-acetyl-β-D-glucopyranoside 在 乙酸酐 、 二甲基亚砜 作用下， 反应 16.0h， 以32%的产率得到(N-propargylcarbamoyl)methyl 3,6-di-O-acetyl-4-deoxy-β-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
• 作为产物：
  描述：

  carboxymethyl-3,4,6-tri-O-acetyl-β-D-glucopyranoside-2-O-lactone 、 炔丙胺 以88%的产率得到(N-propargylcarbamoyl)methyl 3,4,6-tri-O-acetyl-β-D-glucopyranoside
  参考文献：
  名称：

  Carboxymethyl glycoside lactone (CMGL) synthons: Scope of the method and preliminary results on step growth polymerization of α-azide-ω-alkyne glycomonomers

  摘要：

  羧甲基糖苷内酯（CMGLs）是双环合成单体，能迅速打开以获取新型伪糖苷结合物，如糖-氨基酸杂交物、新型糖脂、伪二糖和膜成像系统。经过内酯开环后，自由的OH-2可用于进一步的功能化，生成1,2-双官能化衍生物。本文中通过一种新型的AB型聚合系统进行了说明，该系统具有叠氮和炔烃功能，来源于α或β葡萄糖-CMGL合成单体。在内酯与丙炔胺反应后，通过两种不同的序列引入了叠氮基团，得到了2-甘露糖叠氮或6-葡萄糖叠氮产物。这些AB单体通过铜(I)催化的炔烃-叠氮环加成反应（CuAAC）进行分步增长聚合的能力得到了证实，从而生成了糖聚三嗪。

  DOI：

  10.1007/s11426-010-4058-0