2,3-di-O-benzyl-α-D-arabinofuranosyl-(1->3)-[2,3-di-O-benzyl-α-D-arabinofuranosyl-(1->5)]-1,2-O-isopropylidene-β-D-arabinofuranose | 886852-40-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3-di-O-benzyl-α-D-arabinofuranosyl-(1->3)-[2,3-di-O-benzyl-α-D-arabinofuranosyl-(1->5)]-1,2-O-isopropylidene-β-D-arabinofuranose
• CAS: 886852-40-0
• 化学式: C₄₆H₅₄O₁₃
• 分子量: 814.927
• InChiKey: KDXIBMQLEKZSQS-NHSUZKSTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.04
• 重原子数：
  59.0
• 可旋转键数：
  19.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  141.99
• 氢给体数：
  2.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  2,3-di-O-benzyl-α-D-arabinofuranosyl-(1->3)-[2,3-di-O-benzyl-α-D-arabinofuranosyl-(1->5)]-1,2-O-isopropylidene-β-D-arabinofuranose 、 对甲苯磺酰氯 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以67%的产率得到2,3-di-O-benzyl-5-O-p-toluenesulfonyl-α-D-arabinofuranosyl-(1->3)-[2,3-di-O-benzyl-5-O-p-toluenesulfonyl-α-D-arabinofuranosyl-(1->5)]-1,2-O-isopropylidene-β-D-arabinofuranose
  参考文献：
  名称：

  Synthesis and TNF-α inducing activities of mycoloyl-arabinan motif of mycobacterial cell wall components

  摘要：

  The extract of the cell wall skeleton of Bacillus Calmette-Guerin (BCG-CWS) from Mycobacterium bovis is known to be an activator of innate immunity. Synthesis of pentaarabinofuranoside as part of the arabinan moiety of BCG-CWS was achieved by double alpha-arabinofuranosylation followed by double beta-arabinofuranosylation with orthogonally protected donors. Mycolic esters of the arabinan in the terminal lipo-arabinan motif or BCG-CWS were synthesized through alkylation of unprotected mycolic acid with bis- and tetra-tosylates of pentaarabinofuranoside. A series Of compounds Were Subjected to a tumor necrosis factor alpha (TNF-alpha) secretion-inducing assay, disclosing aspects of the structure-activity relationship which Should be useful in finding the site of the activity. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.12.037
• 作为产物：
  描述：

  ethyl 2-O-benzoyl-3-O-benzyl-5-O-tert-butyldiphenylsilyl-1-thio-α-D-arabinofuranoside 在 2,6-二叔丁基-4-甲基吡啶 、 4 A molecular sieve 、 四丁基氟化铵 、 sodium methylate 、 sodium hydride 、 三氟甲烷磺酸甲酯 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 11.0h， 生成 2,3-di-O-benzyl-α-D-arabinofuranosyl-(1->3)-[2,3-di-O-benzyl-α-D-arabinofuranosyl-(1->5)]-1,2-O-isopropylidene-β-D-arabinofuranose
  参考文献：
  名称：

  Synthesis and TNF-α inducing activities of mycoloyl-arabinan motif of mycobacterial cell wall components

  摘要：

  The extract of the cell wall skeleton of Bacillus Calmette-Guerin (BCG-CWS) from Mycobacterium bovis is known to be an activator of innate immunity. Synthesis of pentaarabinofuranoside as part of the arabinan moiety of BCG-CWS was achieved by double alpha-arabinofuranosylation followed by double beta-arabinofuranosylation with orthogonally protected donors. Mycolic esters of the arabinan in the terminal lipo-arabinan motif or BCG-CWS were synthesized through alkylation of unprotected mycolic acid with bis- and tetra-tosylates of pentaarabinofuranoside. A series Of compounds Were Subjected to a tumor necrosis factor alpha (TNF-alpha) secretion-inducing assay, disclosing aspects of the structure-activity relationship which Should be useful in finding the site of the activity. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.12.037