5-methoxycarbonylpentyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside | 246855-90-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 5-methoxycarbonylpentyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside
• 英文别名: methyl 6-[(2R,3R,4S,5R,6R)-3,4-diacetyloxy-6-(acetyloxymethyl)-5-[(2S,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]oxyhexanoate
• CAS: 246855-90-3
• 化学式: C₃₃H₄₈O₂₀
• 分子量: 764.732
• InChiKey: WQGVPDWFOFOECX-RKWCTXIWSA-N

物化性质

• 沸点：
  729.1±60.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  53
• 可旋转键数：
  26
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  247
• 氢给体数：
  0
• 氢受体数：
  20

反应信息

• 作为反应物：
  描述：

  5-methoxycarbonylpentyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside 在 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 3.0h， 以86%的产率得到5-methoxycarbonylpentyl β-D-galactopyranosyl-(1->4)-β-D-glucopyranoside hemihydrate
  参考文献：
  名称：

  重新审视通过二烷基方酸化学制备糖缀合物。

  摘要：

  乳糖的甲基 6-羟基己酰基糖苷分别用 1,2-二氨基乙烷或肼水合物处理，相应的氨基酰胺 4 和酰肼 13 分别用方酸二甲酯、二乙酯、二丁酯和二癸酯处理。使用 0.05 和 0.5M pH 9 硼酸盐缓冲液，将单酯以不同浓度的半抗原与牛血清白蛋白 (BSA) 缀合。当缀合在更高浓度的半抗原和缓冲液下进行时，更快地实现最大负载，并且缀合效率更高。涉及由酰肼 13 制备的半抗原 14-17 的偶联通常比使用由氨基酰胺 4 制备的化合物 5-8 的偶联更慢且效率更低。发现在缀合过程中保持 pH 值 9 是确保缀合过程快速、高效和可重复的最重要因素。当反应过程中结合混合物的pH值下降，导致反应速率降低甚至结合过程终止时，可以通过加入缓冲盐来恢复结合过程的正常过程。在共轭条件下用氨基酰胺 4 形成的单酯的水解研究表明，癸酯 8 是最稳定的，而甲基化合物 5 是最容易水解的。由酰肼 13 制备的单酯的稳定性与由

  DOI：

  10.1016/j.carres.2007.10.015
• 作为产物：
  描述：

  6-羟基己酸甲酯 、 2,3,6,2',3',4',6'-hepta-O-acetyl-α-D-lactosyl trichloroacetimidate 在 高氯酸 作用下， 以 二氯甲烷 为溶剂， 以84%的产率得到5-methoxycarbonylpentyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside
  参考文献：
  名称：

  HClO4–SiO2 catalyzed glycosylation using sugar trichloroacetimidates as glycosyl donors

  摘要：

  Silica-supported perchloric acid (HClO4-SiO2) has been used as an efficient promoter,, as a replacement of TMSOTf, in various glycosylation reactions using sugar trichloroacetimidates as glycosyl donors. Operational simplicity, economic considerations, high yield, short reaction time and low toxicity were the key features associated with this protocol. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.11.025

文献信息

• Bacteria targeted by human natural antibodies using α-gal conjugated receptor-specific glycopolymers
  作者：Jun Li、Sima Zacharek、Xi Chen、Jianqiang Wang、Wei Zhang、Adam Janczuk、Peng George Wang

  DOI：10.1016/s0968-0896(99)00099-1

  日期：1999.8

  Synthesis of polymerizable beta-lactosyl, Gal alpha 1-->3Gal and alpha-mannosyl acrylamide derivatives with either a hydrophobic aromatic spacer or a hydrophilic biocompatible oligoethoxyl spacer was accomplished. Radical terpolymerizations of beta-lactosyl monomer, alpha-mannosyl monomer, and acrylamide were conducted in aqueous media with ammonium persulfate and N,N,N,N'-tetramethylethylenediamine as initiators. The resulting water soluble glycopolymers were further transformed efficiently by a recombinant alpha 1-->3 galactosyltransferase to afford mediators bearing Gal alpha 1-->3Gal termini as xenoactive antigens and alpha-mannosyl termini as specific ligands for bacterial cells. The binding of the resulting multivalent glycopolymer to bacteria was tested by its ability to inhibit agglutination of yeast to E. coli. The binding of human natural anti-Gal antibodies to the alpha-Gal containing glycopolymers and a monovalent alpha-Gal-Man glycoconjugate was demonstrated by an ELISA inhibition assay. (C) 1999 Elsevier Science Ltd. All rights reserved.