1-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyloxy)-2-hydroxyethane | 35023-69-9

• 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: 1-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyloxy)-2-hydroxyethane
• 英文别名: 2-hydroxyethyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside；2-hydroxyethyl-2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside；1-O-β-D-Tetraacetylgalactopyranosylaethylenglykol；[(2R,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-(2-hydroxyethoxy)oxan-2-yl]methyl acetate
• CAS: 35023-69-9；91364-05-5；55062-10-7
• 化学式: C₁₆H₂₄O₁₁
• 分子量: 392.36
• InChiKey: FGWDENPSBRTVSA-LYYZXLFJSA-N

物化性质

• 熔点：
  101-103 °C
• 沸点：
  475.5±45.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  27
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  144
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  1-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyloxy)-2-hydroxyethane 在 sodium methylate 作用下， 以 吡啶 、 甲醇 为溶剂， 反应 6.33h， 生成 1-(β-D-galactopyranosyloxy)-2-(methanesulfonyloxy)ethane
  参考文献：
  名称：

  Synthesis and NMR characterization of hydroxyurea and mesylglycol glycoconjugates as drug candidates for targeted cancer chemotherapy

  摘要：

  Tumor targeting of glycoconjugated antineoplastic agents is a strategy currently under investigation for cancer chemotherapy. We have synthesized the glucosides and galactosides of the clinically established drug hydroxyurea and of mesylglycol, the reactive moiety of the anticancer drug busulfan. Glycosides of hydroxyurea were obtained by carbamoylation of hydroxylamine glycosides. The glycosides of mesylglycol were synthesized by mesylation of protected glycol glycosides. All compounds were characterized by detailed H-1 and C-13 NMR analysis. (C) 2004 Published by Elsevier Ltd.

  DOI：

  10.1016/j.carres.2004.11.024
• 作为产物：
  描述：

  2-<(4-Methoxybenzyl)oxy>ethyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 生成 1-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyloxy)-2-hydroxyethane
  参考文献：
  名称：

  Synthesis of Biologically Active Sialyl Lewis X Mimetics

  摘要：

  The design and synthesis of two sialyl Lewis X (SLe(x)) mimetics are described. In the design of mimetic 1, an ethylene glycol linkage is used to bridge the fucose and galactose moiety, and a carboxymethyl group is placed in the 3-OH position of the galactose residue to provide the negative charge which is believed to be essential for binding to (E)-selectin. In the design of mimetic 2, a D-tartaric acid derivative is used to provide the trans-dihydroxyl groups originally from the glucosamine moiety for the linkage of the fucose and the carboxypentyl groups. At a concentration of 1.5 mM, 1 inhibits 50% of the binding of SLe(x) glycoconjugate to immobilized recombinant (E)-selectin, while 2 has an IC50 of 10 mM. Mimetic 1 is also found to be stable toward alpha-L-fucosidase. Results from the ROESY and COSY experiments indicate that compound 1 is conformationally flexible, which may explain its relatively weak activity compared to SLe(x) (IC50 = 0.8 mM).

  DOI：

  10.1021/jo00115a027

文献信息

• N-Arylimidazole synthesis by cross-cycloaddition of isocyanides using a novel catalytic system
  作者：Marc-André Bonin、Denis Giguère、René Roy

  DOI：10.1016/j.tet.2007.03.152

  日期：2007.6

  catalytic synthesis of N-arylimidazoles starting from the corresponding N-arylformamides and N-formylglycine esters is described. Application to different aryl substituted electron-withdrawing and -donating groups provided the analogous heterocyclic compounds in very high yields. The use of copper(I) oxide/proline catalysts allowed the reactions to proceed at room temperature. The first synthesis of N-arylimidazole

  的直接催化合成Ñ -arylimidazoles从相应的起始Ñ -arylformamides和Ñ甲酰甘氨酸酯进行说明。应用于不同的芳基取代的吸电子和供电子基团以非常高的产率提供了类似的杂环化合物。使用氧化铜（I）/脯氨酸催化剂可使反应在室温下进行。还描述了带有N-芳基咪唑的碳水化合物部分的第一合成。
• A tetrazine templated method for the synthesis of ternary conjugates
  作者：Boddu Venkateswara Rao、Snehal Dhokale、Pattuparambil R. Rajamohanan、Srinivas Hotha

  DOI：10.1039/c3cc46634e

  日期：——

  Conjugation is an important reaction that enables coupling of molecules. Many protocols exist for the synthesis of binary conjugates from two different molecules or for the polyvalent display of a single molecule. There aren't many methods for the synthesis of ternary conjugates. However, methods for ternary conjugation are important for understanding the interplay of interactions between three biomolecules (or any three molecules per se). A strategy for ternary bioconjugation using inverse electron demand Diels–Alder reaction with tetrazine is studied. Ternary conjugation was demonstrated by the reaction of a model glyco-peptide binary conjugate with a fluorescent tagged olefin.

  共轭反应是一种重要的反应，能够实现分子的耦合。存在许多用于合成两种不同分子之间的二元共轭物或单个分子的多位展示的方案。但对于合成三元共轭物的方法并不多。然而，三元共轭的方法对于理解三个生物分子（或任意三个分子本身）之间的相互作用至关重要。研究了一种利用逆电子需求Diels-Alder反应与四唑进行三元生物共轭的策略。通过模型糖肽二元共轭物与荧光标记的烯烃之间的反应，展示了三元共轭。
• Experimental Measurement of Carbohydrate-Aromatic Stacking in Water by Using a Dangling-Ended DNA Model System
  作者：Juan C. Morales、José J. Reina、Irene Díaz、Anna Aviñó、Pedro M. Nieto、Ramón Eritja

  DOI：10.1002/chem.200800335

  日期：2008.9.8

  fundamental importance for a large number of biological processes; carbohydrate-aromatic stacking is a widespread, but poorly understood, structural motif in this recognition. We describe, for the first time, the measurement of carbohydrate-aromatic interactions from their contribution to the stability of a dangling-ended DNA model system. We observe clear differences in the energetics of the interactions

  蛋白质碳水化合物的识别对于许多生物学过程至关重要。在这种认识中，碳水化合物-芳香族堆积是一种广泛的但了解很少的结构基序。我们第一次描述了碳水化合物-芳香族相互作用对悬挂端DNA模型系统稳定性的贡献的测量。我们观察到几种单糖与苯部分相互作用的能量学上存在明显差异，具体取决于羟基数，立体化学和吡喃糖环中甲基的存在。岩藻糖-苯对是所研究系列中最稳定的（-0.4 Kcal mol（-1）），并且该相互作用与其他与蛋白质芳香族残基（例如Phe-Phe， Phe-Met，或Phe-His。涉及的非共价力似乎是分散力和非常规的氢键，而疏水作用似乎并不驱动相互作用。
• Synthesis and Biophysical Investigations of Oligonucleotides Containing Galactose-Modified DNA, LNA, and 2′-Amino-LNA Monomers
  作者：Annika Ries、Rajesh Kumar、Chenguang Lou、Tamer Kosbar、Empar Vengut-Climent、Per T. Jørgensen、Juan C. Morales、Jesper Wengel

  DOI：10.1021/acs.joc.6b01917

  日期：2016.11.18

  thymidine, LNA-T, and 2′-amino-LNA-T nucleosides were synthesized, converted into the corresponding phosphoramidite derivatives and introduced into short oligonucleotides. Compared to the unmodified control strands, the galactose-modified oligonucleotides in general, and the N2′-functionalized 2′-amino-LNA derivatives in particular, showed improved duplex thermal stability against DNA and RNA complements

  合成半乳糖修饰的胸苷，LNA-T和2'-氨基-LNA-T核苷，将其转化为相应的亚磷酰胺衍生物，并引入短的寡核苷酸中。与未修饰的对照链相比，一般而言，半乳糖修饰的寡核苷酸，尤其是N2'-官能化的2'-氨基-LNA衍生物，对DNA和RNA补体的双链热稳定性提高，并且能够识别错配。此外，2'-氨基-LNA-T衍生物诱导了显着的3'-核酸外切酶抗性。使用分子模型研究进一步研究了这些结果。
• Chemoselective Staudinger-phosphite reaction of symmetrical glycosyl-phosphites with azido-peptides and polygycerols
  作者：Verena Böhrsch、Thresen Mathew、Maximilian Zieringer、M. Robert J. Vallée、Lukas M. Artner、Jens Dernedde、Rainer Haag、Christian P. R. Hackenberger

  DOI：10.1039/c2ob25207d

  日期：——

  In this paper we present the synthesis of glyco-phosphoramidate conjugates as easily accessible analogs of glyco-phosphorous esters via the Staudinger-phosphite reaction. This protocol takes advantage of synthetically accessible symmetrical carbohydrate phosphites in good overall yields, in which ethylene or propylene linkers can be introduced between phosphorous and galactose or lactose moieties. The phosphites were finally applied for the chemoselective reaction with azido-peptides and polyazido(poly)glycerols.

  在本文中，我们展示了通过斯托丁格-磷酸酯反应合成糖基-磷氨酯 conjugates，作为糖基-磷酸酯的易得类似物。该方案利用了合成上易得的对称碳水化合物磷酸酯，且总体产率良好，其中可以在磷和半乳糖或乳糖基之间引入乙烯或丙烯链。最终，磷酸酯被应用于与叠氮肽和聚叠氮（聚）甘油的化学选择性反应。