(N-allylcarbamoyl)methyl 3,4,6-tri-O-acetyl-α-D-glucopyranoside | 1072914-51-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (N-allylcarbamoyl)methyl 3,4,6-tri-O-acetyl-α-D-glucopyranoside
• 英文别名: (N-allylcabamoyl)methyl 3,4,6-tri-O-acetyl-α-D-glucopyranoside；[(2R,3R,4R,5R,6S)-3,4-diacetyloxy-5-hydroxy-6-[2-oxo-2-(prop-2-enylamino)ethoxy]oxan-2-yl]methyl acetate
• CAS: 1072914-51-2
• 化学式: C₁₇H₂₅NO₁₀
• 分子量: 403.386
• InChiKey: DZQXDSWXPCQACD-NHMWIVBRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  28
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  147
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (N-allylcarbamoyl)methyl 3,4,6-tri-O-acetyl-α-D-glucopyranoside 在 Hoveyda-Grubbs catalyst second generation 作用下， 以 二氯甲烷 为溶剂， 以71 %的产率得到
  参考文献：
  名称：

  糖类固醇合成中的钌基交叉复分解

  摘要：

  发表于国际有机制剂和程序：有机合成新期刊（印刷前，2022 年）

  DOI：

  10.1080/00304948.2022.2132804
• 作为产物：
  描述：

  丙烯胺 、 3,4,6-tri-O-acetyl carboxymethyl-α-D-glucopyranoside-2-O-lactone 以 二氯甲烷 为溶剂， 反应 12.0h， 以92%的产率得到(N-allylcarbamoyl)methyl 3,4,6-tri-O-acetyl-α-D-glucopyranoside
  参考文献：
  名称：

  新型单和二糖基羧甲基糖苷内酯（CMGL）的合成及其在1,2-双官能化碳水化合物合成子中的应用

  摘要：

  描述了单和二糖基羧甲基糖苷内酯（CMGLs）的一般和方便访问。通过利用由胺打开CMGL之后在2-位获得的游离OH，报道了一系列新的1,2-双官能化碳水化合物合成子的合成。

  DOI：

  10.1016/j.tetasy.2008.07.016

文献信息

• Self-organizing behaviour of glycosteroidal bolaphiles: insights into lipidic microsegregation
  作者：R. Xu、F. Ali-Rachedi、N. M. Xavier、S. Chambert、F. Ferkous、Y. Queneau、S. J. Cowling、E. J. Davis、J. W. Goodby

  DOI：10.1039/c4ob02191f

  日期：——

  The synthesis of glycosteroidal bolaphile biomimics are described along with the liquid-crystalline behaviours as a function of increasing aliphatic composition.

  描述了糖甾类博拉菲生物模拟物的合成，以及液晶行为随着脂肪族成分增加而变化的情况。
• The unusual self-organising behaviour of a glycosteroidal bolaphile
  作者：Fahima Ali Rachedi、Stéphane Chambert、Fouad Ferkous、Yves Queneau、Stephen J. Cowling、John W. Goodby

  DOI：10.1039/b908235b

  日期：——

  In this communication we report on the self-organising properties of a novel asymmetric bolaphile composed of sugar and steroidal units. The material was found to exhibit unusual phase changes in that it formed a cubic phase upon heating, whereas upon cooling it formed a lamellar phase. This change in property was ascribed to kinetic versus thermodynamic behaviour at the phase transition to the liquid.

  在这篇通讯中，我们报告了一种由糖和甾体单元组成的新型不对称萘酚的自组织特性。研究发现，这种材料表现出不寻常的相变，即在加热时形成立方相，而在冷却时形成薄片相。这种性质变化归因于向液体相变时的动力学行为和热力学行为。
• 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.