3-benzyloxy-2,2-dihexadecyloxymethylpropyl 6-O-benzoyl-2,3-di-O-benzyl-β-D-mannopyranosyl-(1->4)-6-O-benzoyl-2,3-di-O-benzyl-β-D-mannopyranoside | 1006589-10-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-benzyloxy-2,2-dihexadecyloxymethylpropyl 6-O-benzoyl-2,3-di-O-benzyl-β-D-mannopyranosyl-(1->4)-6-O-benzoyl-2,3-di-O-benzyl-β-D-mannopyranoside
• CAS: 1006589-10-1
• 化学式: C₉₈H₁₃₄O₁₆
• 分子量: 1568.13
• InChiKey: ZRKDUENXTHMZAY-CPVMBWSSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  21.45
• 重原子数：
  114.0
• 可旋转键数：
  61.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  174.36
• 氢给体数：
  1.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  3-benzyloxy-2,2-dihexadecyloxymethylpropyl 6-O-benzoyl-2,3-di-O-benzyl-β-D-mannopyranosyl-(1->4)-6-O-benzoyl-2,3-di-O-benzyl-β-D-mannopyranoside 、 2,3-双-O-(苯基甲基)-4,6-O-[(R)-苯基亚甲基]-1-硫代- a-D--吡喃甘露糖苷苯酯 在 2,6-二叔丁基-4-甲基吡啶 、 1-(苯基亚硫酰基)哌啶 、 trifluoromethanesulfonic acid anhydride 作用下， 以 二氯甲烷 为溶剂， 反应 2.08h， 以51%的产率得到3-benzyloxy-2,2-dihexadecyloxymethylpropyl 2,3-di-O-benzyl-4,6-di-O-benzylidene-β-D-mannopyranosyl-(1->4)-6-O-benzoyl-2,3-di-O-benzyl-β-D-mannopyranosyl-(1->4)-6-O-benzoyl-2,3-di-O-benzyl-β-D-mannopyranoside
  参考文献：
  名称：

  Synthesis of β-(1→4)-oligo-d-mannuronic acid neoglycolipids

  摘要：

  Mammalian Toll-like receptors (TLRs) play important roles in host immune defense. The activation of TLR and downstream signaling pathways have great impact on human physiology. Chemically diverse microbial products as well as synthetic ligands serve as agonists for these receptors. Recently, synthetic TLR ligands are being exploited as useful therapeutic agents for a variety of diseases including infections, inflammatory diseases, and cancers. Alginate polymers and oligosaccharides are strong immune stimulants mediated by TLR2/4, but synthesis of alginate oligomers is rarely studied. Reported here are the design and chemical synthesis of two beta-(1 -> 4)-di- and beta-(1 -> 4)-tri-D-mannuronic acid neoglycolipids 1 and 2 as potential TLR ligands. By using 4,6-di-O-benzylidene-protected 1-thio mannoside 7 as a glycosyl donor, the diastereoselective beta-D-mannosylation protocol provides the beta-(1 -> 4)-D-mannobiose and beta-(1 -> 4)-D-mannotriose derivatives, which upon regioselective oxidation with TEMPO/BAIB oxidation system yield the corresponding beta-(1 -> 4)-D-mannuronic acid containing neoglycolipids 1 and 2. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2007.10.007
• 作为产物：
  描述：

  3-benzyloxy-2,2-dihexadecyloxymethylpropyl 2,3-di-O-benzyl-β-D-mannopyranosyl-(1->4)-6-O-benzoyl-2,3-di-O-benzyl-β-D-mannopyranoside 、 苯甲酰氯 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 以94%的产率得到3-benzyloxy-2,2-dihexadecyloxymethylpropyl 6-O-benzoyl-2,3-di-O-benzyl-β-D-mannopyranosyl-(1->4)-6-O-benzoyl-2,3-di-O-benzyl-β-D-mannopyranoside
  参考文献：
  名称：

  Synthesis of β-(1→4)-oligo-d-mannuronic acid neoglycolipids

  摘要：

  Mammalian Toll-like receptors (TLRs) play important roles in host immune defense. The activation of TLR and downstream signaling pathways have great impact on human physiology. Chemically diverse microbial products as well as synthetic ligands serve as agonists for these receptors. Recently, synthetic TLR ligands are being exploited as useful therapeutic agents for a variety of diseases including infections, inflammatory diseases, and cancers. Alginate polymers and oligosaccharides are strong immune stimulants mediated by TLR2/4, but synthesis of alginate oligomers is rarely studied. Reported here are the design and chemical synthesis of two beta-(1 -> 4)-di- and beta-(1 -> 4)-tri-D-mannuronic acid neoglycolipids 1 and 2 as potential TLR ligands. By using 4,6-di-O-benzylidene-protected 1-thio mannoside 7 as a glycosyl donor, the diastereoselective beta-D-mannosylation protocol provides the beta-(1 -> 4)-D-mannobiose and beta-(1 -> 4)-D-mannotriose derivatives, which upon regioselective oxidation with TEMPO/BAIB oxidation system yield the corresponding beta-(1 -> 4)-D-mannuronic acid containing neoglycolipids 1 and 2. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2007.10.007