2,3,4,5-tetra-O-acetyl-p-nitrophenyl-α-D-galactopyranoside | 152704-98-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4,5-tetra-O-acetyl-p-nitrophenyl-α-D-galactopyranoside
• 英文别名: 2,3,4,6-tetra-O-acetyl-p-aminophenyl-α-D-galactopyranoside；p-aminophenyl-2,3,4,6-tetraacetyl-α-D-galactopyranoside；[(2R,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-(4-aminophenoxy)oxan-2-yl]methyl acetate
• CAS: 152704-98-8
• 化学式: C₂₀H₂₅NO₁₀
• 分子量: 439.419
• InChiKey: BXZPMBDMUIOXQQ-CXQPBAHBSA-N

物化性质

• 沸点：
  540.3±50.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  31
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  150
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  2,3,4,5-tetra-O-acetyl-p-nitrophenyl-α-D-galactopyranoside 在 4-二甲氨基吡啶 、 sodium methylate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 p-(tetradecanoylamido)phenyl-α-D-galactopyranoside
  参考文献：
  名称：

  Carbohydrate mediated drug delivery: Synthesis and characterization of new lipid-conjugates

  摘要：

  A new synthetic methodology for cationic glycolipids using p-aminophenyl-alpha-D-mannopyranoside (PAPM) and p-aminophenyl-alpha-D-galactopyranoside (PAPG) with spacer in between the quaternary nitrogen atom and the sugar unit is developed. In addition, a new class of neutral glycolipid conjugates, such as PAPM-lipids or PAPG-lipids conjugates was also synthesized for targeting drugs to receptors. The precipitation-inhibition assay showed that conjugate of PAPM inhibited the concanavalin A and invertase aggregation. This binding inhibition study of a synthesized compound suggests that conjugates of PAPM can be potentially used to target mannose receptors. In addition, a higher transfection was obtained by mixing PAPM with pSV-beta-gal reporter gene and incubating with mannose binding protein/receptor expressing A549 cells. The coexistence of both mannose group and a net positive charge may result in improved transfection efficiency in cells expressing mannose binding proteins/receptors. (C) 2014 Elsevier Ireland Ltd. All rights reserved.

  DOI：

  10.1016/j.chemphyslip.2014.10.003
• 作为产物：
  描述：

  4-硝基苯基-α-D-吡喃半乳糖苷 在 palladium on activated charcoal 吡啶 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 9.0h， 生成 2,3,4,5-tetra-O-acetyl-p-nitrophenyl-α-D-galactopyranoside
  参考文献：
  名称：

  糖基卟啉有机凝胶中原硅酸四乙酯（TEOS）的溶胶-凝胶缩聚：通过溶胶-凝胶转录过程将糖定向的卟啉纤维库进行无机转化。

  摘要：

  在其外围具有单糖基团的加糖卟啉（1 ae）已被合理地设计用于新型胶凝剂。这些化合物中的一些倾向于形成足够稳定的一维聚集体，以显示对DMF-醇混合溶剂的成功胶凝能力。特定柱状上部结构中的聚集模式已通过紫外可见光谱（UV / Vis），圆二色性（CD），扫描电子显微镜（SEM）和透射电子显微镜（TEM）进行了详细评估。从1 ac获得的加糖的卟啉凝胶的所有紫​​外线可见光谱均显示出Soret带吸收，该吸收移向较低波长并显着加宽。这种现象表明，这些卟啉核以H聚集的方式彼此强烈相互作用，它驱动一维卟啉堆叠阵列的产生。来自1 a和1 b的有机凝胶的CD光谱（呈异构体形式）显示出几乎对称的图案，而来自1 c的凝胶给出的图案却完全不同。这意味着凝胶原纤维以右旋或左旋方式缠绕。这反映了胶凝剂特定分子结构中的手性。凝胶纤维的SEM结果与CD谱图非常吻合。1 a中的凝胶原纤维具有左旋螺旋，而1 b中的凝胶原纤维

  DOI：

  10.1002/chem.200305042

文献信息

• Resolution of Enantiomers Using Sugar-Carrying Polyisocyanides as Chiral Stationary Phases for HPLC
  作者：Akiko Tsuchida、Teruaki Hasegawa、Kazukiyo Kobayashi、Chiyo Yamamoto、Yoshio Okamoto

  DOI：10.1246/bcsj.75.2681

  日期：2002.12

  derivatives of α-/β-glucose and α-/β-galactose-carrying helical poly(phenyl isocyanide)s were used as chiral stationary phases (CSPs) for HPLC to estimate their chiral recognition abilities. CD spectroscopy suggested that the helix sense in these rigid helical polymers may be regulated by the chirality of the α- or β-anomeric center of the sugar moieties. Some 10 different types of racemates with functional

  3,5-二甲基苯基氨基甲酸酯衍生物的α-/β-葡萄糖和携带α-/β-半乳糖的螺旋聚（苯基异氰）被用作HPLC的手性固定相（CSP），以评估它们的手性识别能力。CD 光谱表明，这些刚性螺旋聚合物中的螺旋意义可能受糖部分 α-或 β-异头中心的手性调节。取决于悬垂糖的立体结构，大约 10 种不同类型的具有官能团的外消旋物被完全或部分解析。增强的手性识别能力归因于沿螺旋骨架的三维调控的糖阵列；也就是说，携带 α-葡萄糖的螺旋聚（苯基异氰）的 CSP 比相应的柔性聚（N-苯基丙烯酰胺）的 CSP 表现出更有效的对映分离。
• Generation and screening of a dynamic combinatorial library
  申请人：Therascope AG

  公开号：EP1130009A1

  公开（公告）日：2001-09-05

  The present invention concerns a method for selectively establishing a dynamic combinatorial library of ligands binding to a target which binds at least two functionalities, which method comprises the following steps: selecting a plurality of functionalities which upon combination with each other are capable of forming an antity which may bind to the at least two functionalities in the target; linking at least two identical or different functionalities by at least one spacer group allowing reversible bond formation, thus creating discrete ligands; mixing together a plurality of a different discrete ligands having different combinations of functionalities; subjecting the mixture to conditions allowing a reversible bond formation and cleavage, hence a scrambling of the formalities; analyzing the mixture obtained; adding the target to the mixture; again analyzing the mixture, comparing the results obtained and identifying the functionality combinations which are most appropriate for the formation of a bond. In a further embodiment of the invention, the target is added when the discrete ligands are mixed together, in order to be present when the scrambling takes place.

  本发明涉及一种选择性地建立与至少两种功能结合的靶标结合配体动态组合库的方法，该方法包括以下步骤： 选择多个官能团，这些官能团相互组合后能够形成一个反体，该反体可与靶标中的至少两个官能团结合； 用至少一个间隔基团将至少两个相同或不同的官能团连接起来，形成可逆键，从而形成离散配体； 将具有不同官能团组合的多种不同离散配体混合在一起； 将混合物置于允许可逆键形成和裂解的条件下，从而扰乱形式； 分析得到的混合物； 将目标物加入混合物中； 再次分析混合物，比较所得结果，确定最适合形成键的官能度组合。 在本发明的另一个实施方案中，目标物是在离散配体混合在一起时加入的，以便在发生扰乱时出现。
• Solution casting method and polymer film
  申请人：Sugiura Masaru

  公开号：US20050077648A1

  公开（公告）日：2005-04-14

  A solvent in which dichloromethane is mixed with alcohol as a poor solvent is used for preparing a dope. Alcohol is supplied to the dope in a inline pipe to mix with a static mixer, such as a casting dope in which a composition of alcohol is increased. The temperature of the rotary drum is adjusted to −7° C. The casting dope is fed from a casting die to the rotary drum so as to form a casting film whose thickness is 40 μm. Since the content of alcohol is high and a storage modulus of the cooled casting film is at least 150 thousands Pa, the peeling defect does not occur, and the stretch is reduced as far as possible. A gel-like film is dried by a tenter type drying device, and stretched such that the stretch ratio is at most 110%. The produced film is thin and excellent in a surface condition and optical isotropy.

  二氯甲烷与作为劣质溶剂的酒精混合的溶剂用于制备涂料。酒精通过内联管道供应到涂料中，与静态混合器混合，如增加酒精成分的铸造涂料。将浇注料从浇注模具送入旋转滚筒，以形成厚度为 40 μm 的浇注膜。由于酒精含量高，冷却后的浇注膜的储存模量至少为 15 万帕，因此不会出现剥离缺陷，拉伸也尽可能减小。凝胶状薄膜由拉幅机干燥，拉伸率不超过 110%。生产出的薄膜很薄，表面状态和光学各向同性都很好。
• GENERATION AND SCREENING OF A DYNAMIC COMBINATORIAL LIBRARY
  申请人：Therascope AG

  公开号：EP1261568A2

  公开（公告）日：2002-12-04
• [EN] GENERATION AND SCREENING OF A DYNAMIC COMBINATORIAL LIBRARY<br/>[FR] SYNTHESE ET CRIBLAGE D'UNE BANQUE COMBINATOIRE DYNAMIQUE
  申请人：THERASCOPE AG

  公开号：WO2001064605A2

  公开（公告）日：2001-09-07

  The present invention concerns a method for selectively establishing a dynamic combinatorial library of ligands for a target which binds at least two functionalities, which method comprises the following steps: selecting a plurality of functionalities which upon combination with each other are capable of forming an entity which may bind to the at least two functionalities in the target; selecting at least one spacer group to be located between the at least two functionalities, which spacer group is of an appropriate size and/or flexibility to allow the functionalities to fit into the binding sites on the target and allowing a reversible bond formation and cleavage; creating discrete ligands by linking at least two identical or different functionalities by at least one spacer group or; linking the functionalities to fragments of the spacer group which contain functions allowing the said reversible bond formation under formation of the spacer group and cleavage of it; mixing together a plurality of different discrete ligands and/or different functionalities; subjecting the mixture to conditions allowing a reversible bond formation and cleavage; adding the target to the mixture; identifying the functionality combinations which are most appropriate for the formation of a complex between the target and the active molecule. In a further embodiment of the invention, the target is added when the discrete ligands are mixed together, in order to be present when the scrambling takes place.