N-maltoheptaosyl-3-acetamido-1-propyne | 1193536-70-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-maltoheptaosyl-3-acetamido-1-propyne
• 英文别名: N-[(2R,3R,4R,5S,6R)-5-[(2R,3R,4R,5S,6R)-5-[(2R,3R,4R,5S,6R)-5-[(2R,3R,4R,5S,6R)-5-[(2R,3R,4R,5S,6R)-5-[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]-N-prop-2-ynylacetamide
• CAS: 1193536-70-7
• 化学式: C₄₇H₇₇NO₃₆
• 分子量: 1232.11
• InChiKey: MJWKJJZYHWBBRF-IKBWQNOVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -15.2
• 重原子数：
  84
• 可旋转键数：
  21
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  585
• 氢给体数：
  22
• 氢受体数：
  36

反应信息

• 作为反应物：
  描述：

  6-叠氮基己酸 、 N-maltoheptaosyl-3-acetamido-1-propyne 在 copper(II) sulfate 、 sodium ascorbate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 24.0h， 生成 6-[4-[[acetyl-[(2R,3R,4R,5S,6R)-5-[(2R,3R,4R,5S,6R)-5-[(2R,3R,4R,5S,6R)-5-[(2R,3R,4R,5S,6R)-5-[(2R,3R,4R,5S,6R)-5-[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]amino]methyl]triazol-1-yl]hexanoic acid
  参考文献：
  名称：

  Synthesis of Silver Glyconanoparticles from New Sugar-Based Amphiphiles and Their Catalytic Application

  摘要：

  Oligosaccharide-based amphiphiles were readily prepared by click chemistry from omega-azido-hexanoic or dodecanoic acids with propargyl-functionalized maltoheptaose or xyloglucanoligosaccharides. These amphiphilic compounds were used as capping/stabilizer agents in order to obtain highly stable catalytic silver glyconanoparticles (Ag-GNPs) through the in situ reduction of silver nitrate with NaBH4. With a view to long-term storage, the stabilization was optimized using a multivariate approach, and the nanoparticles were characterized by UV-vis, TEM, SAXS, and DLS. In order to explore the functionality of the Ag-GNPs in catalysis, a full kinetic analysis of the reduction of p-nitrophenol by NaBH4 in water and in water/ethanol mixtures was performed under semi-heterogeneous and quasi-homogeneous conditions. A pseudomonomolecular surface reaction was performed, and the kinetic data obtained were treated according to the Langmuir model. The Ag-GNPs were very active, and both substrates adsorbed onto the surface of the nanoparticles. For comparison purposes, the reaction was also performed in the presence of silver-sodium dodecanoate nanoparticles, which showed catalytic activity similar to that of the glyconanoparticles, supporting the choice of the carboxyl group as the stabilizing agent, although it provided much lower temporal stability. Finally, by combining kinetic and water/ethanol surface tension data it was possible to observe the effect of the addition of the less polar solvent (ethanol) to the reaction medium.

  DOI：

  10.1021/la501359h
• 作为产物：
  描述：

  、 乙酸酐 以 甲醇 为溶剂， 以8.75 g的产率得到N-maltoheptaosyl-3-acetamido-1-propyne
  参考文献：
  名称：

  Thermoresponsive Vesicular Morphologies Obtained by Self-Assemblies of Hybrid Oligosaccharide-block-poly(N-isopropylacrylamide) Copolymer Systems

  摘要：

  This work discusses the self-assembly properties of thermoresponsive hybrid oligosaccharide-block-poly(N-isopropylacrylamide) copolymer systems: maltoheptase-block-poly(N-isopropylacrylamide) (Mal(7)-b-PNIPAM(n)) copolymers. Those systems at different molar masses and volume fractions were synthesized Using Cu(I)-catalyzed 1,3-dipolar azide/alkyne cycloaddition, so-called "click" chemistry, between an alkynyl-functionalized maltoheptaose (I) and poly(N-isopropylacrylamide) having a terminal azido group (N-3-PNIPAM(n)) prepared by atom transfer radical polymerization (ATRP). While the cloud point (T-cp) of the N-3-PNIPAM(n) ranged from 36.4 to 51.5 degrees C depending on the degree of polymerization, those obtained of the diblock copolymers ranged from 39.4 to 73.9 degrees C. The self-assembly of such systems is favored due to the hydrophobicity of the PNIPAM in water above the T-cp. While the N-3-PNIPAM(n) present polydisperse globular shape with a mean diameter of 500 nm, well-defined vesicular morphologies with an approximate diameter of 300 nm are obtained in diblock copolymer systems. These results were obtained and confirmed using static and dynamic light scattering as well as imaging techniques such as transmission electron microscope experiments.

  DOI：

  10.1021/la902743y

文献信息

• Synthesis of Oligosaccharide-Based Block Copolymers with Pendent π-Conjugated Oligofluorene Moieties and Their Electrical Device Applications
  作者：Han-Sheng Sun、Yu-Cheng Chiu、Wen-Ya Lee、Yougen Chen、Akira Hirao、Toshifumi Satoh、Toyoji Kakuchi、Wen-Chang Chen

  DOI：10.1021/acs.macromol.5b00651

  日期：2015.6.23

  We report the synthesis and electric device applications of oligosaccharide-based diblock copolymers consisting of a maltoheptaose (MH) block and a poly(4-oligofluorenylstyrene) block (PStFl(n), n = 1 or 2), referred to as MH-b-PStFl(n). MH-b-PStFl(n) was prepared by the Cu(I)-catalyzed click reaction of azido-terminated PStFl(n) (PStFl(n)-N-3), which was obtained from the azidation reaction of the bromo-terminated PStFl(n) (PStFl(n)-Br), with excess ethynylterminated MH in the THF/DMF mixture solvent. The resulting diblock copolymers self-assembled to spherical microdomains with sub-10 nm sizes in both bulk and thin film state after annealing process. Thereafter, the MH-b-PStFl(n) thin film (similar to 50 nm) with the self-assembled nanoscale spherical aggregates was used as the charge storage layer for the pentacene-based field-effect transistor type memory devices. The MH-b-PStFl(n)-based devices had the excellent hole mobility (0.25-0.52 cm(2) V-1 s(-1)) and the high ON/OFF current (I-ON/I-OFF) ratio of 10(7)-10(8), of which the MH-b-PStFl(1)-based one had the higher mobility than that of the MH-b-PStFl(2)-based one because the pentacene crystal in the former device possessed the larger grain size and fewer boundaries. On the other hand, the MH-b-PStFl(2)-based device showed a larger memory window than the MH-b-PStFl(1)-based one because the stronger electron-donating effect of the difluorenyl group in MH-b-PStFl(2) increased the charge storage capability of its related device. All the memory devices showed a long-term retention time over 10(4) s with the high I-ON/I-OFF ratio of 10(6)-10(8). Among these devices, the MH-b-PStFl(1)-based device showed a good WRER endurance over 180 cycles. This work not only demonstrates the tunable electrical memory characteristics by adjusting the pi-conjugation length of the oligofluorenyl side chain in the polymer electret but also provides a promising approach for developing the next-generation "green electronics" using natural materials.
• Synthesis of Silver Glyconanoparticles from New Sugar-Based Amphiphiles and Their Catalytic Application
  作者：Renato Eising、Welman C. Elias、Brunno L. Albuquerque、Sébastien Fort、Josiel B. Domingos

  DOI：10.1021/la501359h

  日期：2014.6.3

  Oligosaccharide-based amphiphiles were readily prepared by click chemistry from omega-azido-hexanoic or dodecanoic acids with propargyl-functionalized maltoheptaose or xyloglucanoligosaccharides. These amphiphilic compounds were used as capping/stabilizer agents in order to obtain highly stable catalytic silver glyconanoparticles (Ag-GNPs) through the in situ reduction of silver nitrate with NaBH4. With a view to long-term storage, the stabilization was optimized using a multivariate approach, and the nanoparticles were characterized by UV-vis, TEM, SAXS, and DLS. In order to explore the functionality of the Ag-GNPs in catalysis, a full kinetic analysis of the reduction of p-nitrophenol by NaBH4 in water and in water/ethanol mixtures was performed under semi-heterogeneous and quasi-homogeneous conditions. A pseudomonomolecular surface reaction was performed, and the kinetic data obtained were treated according to the Langmuir model. The Ag-GNPs were very active, and both substrates adsorbed onto the surface of the nanoparticles. For comparison purposes, the reaction was also performed in the presence of silver-sodium dodecanoate nanoparticles, which showed catalytic activity similar to that of the glyconanoparticles, supporting the choice of the carboxyl group as the stabilizing agent, although it provided much lower temporal stability. Finally, by combining kinetic and water/ethanol surface tension data it was possible to observe the effect of the addition of the less polar solvent (ethanol) to the reaction medium.
• Thermoresponsive Vesicular Morphologies Obtained by Self-Assemblies of Hybrid Oligosaccharide-<i>block</i>-poly(<i>N</i>-isopropylacrylamide) Copolymer Systems
  作者：Issei Otsuka、Keita Fuchise、Sami Halila、Sébastien Fort、Karim Aissou、Isabelle Pignot-Paintrand、Yougen Chen、Atsushi Narumi、Toyoji Kakuchi、Redouane Borsali

  DOI：10.1021/la902743y

  日期：2010.2.16

  This work discusses the self-assembly properties of thermoresponsive hybrid oligosaccharide-block-poly(N-isopropylacrylamide) copolymer systems: maltoheptase-block-poly(N-isopropylacrylamide) (Mal(7)-b-PNIPAM(n)) copolymers. Those systems at different molar masses and volume fractions were synthesized Using Cu(I)-catalyzed 1,3-dipolar azide/alkyne cycloaddition, so-called "click" chemistry, between an alkynyl-functionalized maltoheptaose (I) and poly(N-isopropylacrylamide) having a terminal azido group (N-3-PNIPAM(n)) prepared by atom transfer radical polymerization (ATRP). While the cloud point (T-cp) of the N-3-PNIPAM(n) ranged from 36.4 to 51.5 degrees C depending on the degree of polymerization, those obtained of the diblock copolymers ranged from 39.4 to 73.9 degrees C. The self-assembly of such systems is favored due to the hydrophobicity of the PNIPAM in water above the T-cp. While the N-3-PNIPAM(n) present polydisperse globular shape with a mean diameter of 500 nm, well-defined vesicular morphologies with an approximate diameter of 300 nm are obtained in diblock copolymer systems. These results were obtained and confirmed using static and dynamic light scattering as well as imaging techniques such as transmission electron microscope experiments.