1,3,4-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranose | 1333211-35-0

• 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: 1,3,4-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranose
• CAS: 1333211-35-0
• 化学式: C₁₅H₂₀Cl₃NO₁₀
• 分子量: 480.684
• InChiKey: FGYIQZOSOCQPRT-SYLRKERUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  29.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  146.69
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  三苯基甲醇 、 1,3,4-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranose 在 三苯基膦双(三氟甲磺酰亚胺)金 作用下， 以 甲苯 为溶剂， 反应 0.5h， 以73%的产率得到(2S,3R,4R,5S,6R)-3-{[(2,2,2-trichloroethoxy)carbonyl]amino}-6-[(trityloxy)methyl]tetrahydro-2H-pyran-2,4,5-triyl triacetate
  参考文献：
  名称：

  金（I）催化的醇类烷基化试剂合成不对称醚

  摘要：

  基于苄基醇，叔丁醇和三苯甲醇作为烷基化试剂的金催化的微波辐射醇保护策略已经被开发出来。对于大多数选定的醇，该保护策略具有宽泛的官能团耐受性和令人满意的产率。在GC-MS技术和化学动力学实验的辅助下，用氧18同位素标记的醇探索了这种转变的机理。该策略为有机合成中的苄基，叔丁基和三苯甲基醚的制备提供了一种有效，直接和替代的方法。

  DOI：

  10.1002/adsc.201401097
• 作为产物：
  描述：

  2-氨基-2-脱氧葡萄糖盐酸盐 在 吡啶 、 水 、 碳酸氢钠 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 19.5h， 生成 1,3,4-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranose
  参考文献：
  名称：

  Preparation, characterization, and biological evaluation of 6I,6IV-di-O-[α-l-fucopyranosyl-(1→6)-2-acetamido-2-deoxy-β-d-glucopyranosyl]-cyclomaltoheptaose and 6-O-[α-l-fucopyranosyl-(1→6)-2-acetamido-2-deoxy-β-d-glucopyranosyl]-cyclomaltoheptaose

  摘要：

  6(I), 6(IV)-Di-O-[alpha-L-fucopyranosyl-(1 -> 6)-2-acetamido-2-deoxy-beta-D-glucopyranosyl]-cyclomaltoheptaose (beta CD) {6(I), 6(IV)-di-O-[alpha-L-Fuc-(1 -> 6)-beta-D-GlcNAc]-beta CD (5)} and 6-O-[alpha-L-fucopyranosyl-(1 -> 6)-2-acetamido-2-deoxy-beta-D-glucopyranosyl]-beta CD {6-O-[alpha-L-Fuc-(1 -> 6)-beta-D-GlcNAc]-beta CD (6)} were chemically synthesized using the corresponding authentic compounds, bis(2,3-di-O-acetyl)-pentakis(2,3,6-tri-O-acetyl)-beta CD as the glycosyl acceptor and 2,3,4-tri-O-benzyl-alpha-L-fucopyranosyl-(1 -> 6)-3,4-di-Oacetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-D-glucopyranosyl trichloroacetimidate as the fuco-glucosaminyl donor. NMR confirmed that alpha-L-Fuc-(1 -> 6)-D-GlcNAc was bonded by beta-linking to the beta CD ring. To evaluate biological efficiency, the biological activities of the new branched beta CDs were examined. The cell detachment activity of 5 was lower than that of 6 in real-time cell sensing (RT-CES) assay, indicating that 5 has lower toxicity. In SPR analysis, 5 had a higher special binding with AAL, a fucose-recognizing lectin. These results suggest that 5 could be an efficient drug carrier directed at cells expressing fucose-binding proteins. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.06.013