8-p-methoxyphenoxyloctyl 2-acetamido-4,6-benzylidene-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2-deoxy-β-D-glucopyranoside | 178986-40-8

• 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: 8-p-methoxyphenoxyloctyl 2-acetamido-4,6-benzylidene-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2-deoxy-β-D-glucopyranoside
• CAS: 178986-40-8
• 化学式: C₄₄H₅₉NO₁₇
• 分子量: 873.949
• InChiKey: YSMTUVMTMLGYCV-JYTUSYSNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.24
• 重原子数：
  62.0
• 可旋转键数：
  21.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  208.14
• 氢给体数：
  1.0
• 氢受体数：
  17.0

反应信息

• 作为反应物：
  描述：

  8-p-methoxyphenoxyloctyl 2-acetamido-4,6-benzylidene-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2-deoxy-β-D-glucopyranoside 在 甲醇 、 sodium methylate 、 溶剂黄146 作用下， 反应 3.0h， 生成 N-[(2R,3R,4R,5S,6R)-5-Hydroxy-6-hydroxymethyl-2-[8-(4-methoxy-phenoxy)-octyloxy]-4-((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-acetamide
  参考文献：
  名称：

  Towards oligosaccharide libraries: A study of the random galactosylation of unprotected N-acetylglucosamine

  摘要：

  A single reaction of an unprotected beta-D-GlcNAc glycoside with tetra-O-acetyl-alpha-D-galactopyranosyl trichloroacetimidate in dioxane, catalyzed by BF3-etherate, was shown to yield all six possible Gal-GlcNAc disaccharides. This result is surprising not only because significant amounts of alpha-linked disaccharides were formed, despite the presence of a participating group at O-2 of the glycosyl donor, but also because glycosylation of the primary OH-6 is not the dominant reaction. These results suggest 'random-glycosylation' to be a valid strategy for the rapid production of oligosaccharide libraries. Copyright (C) 1996 Elsevier Science Ltd.

  DOI：

  10.1016/0968-0896(96)00064-8
• 作为产物：
  描述：

  8-p-methoxyphenoxyloctanol 在 甲醇 、 calcium sulfate 、 sodium methylate 、 氰化汞 、 对甲苯磺酸 作用下， 以 硝基甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 40.0h， 生成 8-p-methoxyphenoxyloctyl 2-acetamido-4,6-benzylidene-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Towards oligosaccharide libraries: A study of the random galactosylation of unprotected N-acetylglucosamine

  摘要：

  A single reaction of an unprotected beta-D-GlcNAc glycoside with tetra-O-acetyl-alpha-D-galactopyranosyl trichloroacetimidate in dioxane, catalyzed by BF3-etherate, was shown to yield all six possible Gal-GlcNAc disaccharides. This result is surprising not only because significant amounts of alpha-linked disaccharides were formed, despite the presence of a participating group at O-2 of the glycosyl donor, but also because glycosylation of the primary OH-6 is not the dominant reaction. These results suggest 'random-glycosylation' to be a valid strategy for the rapid production of oligosaccharide libraries. Copyright (C) 1996 Elsevier Science Ltd.

  DOI：

  10.1016/0968-0896(96)00064-8

文献信息

• Synthesis of Monosulfated Lewis a Trisaccharide Library Through Sulfation of a Partial Protected Trisaccharide
  作者：Yili Ding、Bingyun Wang

  DOI：10.2174/1570178614666170505113336

  日期：2017.6.14

  stimulated much synthetic activity in oligosaccharide synthesis, the sulfate group in sulfated oligosaccharides has been shown to be constitutively involved in the interaction of ligands with selectins, establishing combinatorial methods for the synthesis of sulfated oligosaccharide library may be useful for screening of ligands of selectins. Results: Random sulfation of a partial benzyl protected Lewis

  背景：糖缀合物的生物学意义刺激了寡糖合成中的许多合成活性，已显示硫酸化寡糖中的硫酸基团与配体与选择素的相互作用是组成性参与的，建立用于合成硫酸化寡糖文库的组合方法可能是有用的用于筛选选择素的配体。 结果：吡啶中部分苄基保护的Lewis A三糖的随机硫酸化提供了硫酸化的三糖混合物。用Pd / C氢化并在Sephadex A-50柱上纯化后，获得单硫酸化三糖文库，为混合物。该混合物的HH COZY NMR光谱表明，该混合物包含所有五个可能的具有可接受比率的单硫酸化的路易斯A三糖。 结论：随机硫酸化部分受保护的寡糖是迄今为止合成单硫酸化寡糖文库最有效的方法。