2,3,4-tri-O-benzyl-α-L-fucopyranosyl-(1->6)-3,4-di-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-D-glucopyranosyl trichloroacetimidate | 1333211-33-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4-tri-O-benzyl-α-L-fucopyranosyl-(1->6)-3,4-di-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-D-glucopyranosyl trichloroacetimidate
• CAS: 1333211-33-8
• 化学式: C₄₂H₄₆Cl₆N₂O₁₃
• 分子量: 999.551
• InChiKey: HNFNABWNFRFGMU-QFWPFCICSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.92
• 重原子数：
  63.0
• 可旋转键数：
  17.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  179.39
• 氢给体数：
  2.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  2,3,4-tri-O-benzyl-α-L-fucopyranosyl-(1->6)-3,4-di-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-D-glucopyranosyl trichloroacetimidate 、 C₈₀H₁₀₈O₅₄ 、 乙酸酐 在 三氟甲磺酸三甲基硅酯 、 溶剂黄146 作用下， 以 二氯甲烷 、 四氢呋喃 为溶剂， 反应 3.0h， 以323 mg的产率得到6(I),6(IV)-di-O-[α-L-fucopyranosyl-(1->6)-2-acetamido-2-deoxy-β-D-glucopyranosyl]-βCD
  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
• 作为产物：
  描述：

  6-O-(tert-butyldimethylsilyl)-1,3,4-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranose 在 三氟甲磺酸三甲基硅酯 、 水 、 乙酸肼 、 溶剂黄146 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 2,3,4-tri-O-benzyl-α-L-fucopyranosyl-(1->6)-3,4-di-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-D-glucopyranosyl trichloroacetimidate
  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