(2R,3S,4S,5R,6R)-2-((benzyloxy)methyl)-6-(((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate | 1253857-15-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3S,4S,5R,6R)-2-((benzyloxy)methyl)-6-(((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate
• CAS: 1253857-15-6
• 化学式: C₂₄H₄₂O₁₄
• 分子量: 554.589
• InChiKey: YAEDVRAEESUGBE-XCCNGPICSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.08
• 重原子数：
  38.0
• 可旋转键数：
  13.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  140.22
• 氢给体数：
  1.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  4-硝基邻苯二甲腈 、 (2R,3S,4S,5R,6R)-2-((benzyloxy)methyl)-6-(((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 120.5h， 以79%的产率得到4-(((2R,3S,4S,5R,6R)-3,4,5-tris(methoxymethoxy)-6-(((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyltetrahydro-5H-bis([1,3]dioxolo)[4,5-b:4',5'-d]pyran-5-yl)methoxy)tetrahydro-2H-pyran-2-yl)methoxy)phthalonitrile
  参考文献：
  名称：

  The synthesis and characterisation of carbohydrate-functionalised porphyrazines

  摘要：

  A synthetic pathway to the incorporation of mono- and disaccharide carbohydrate moieties into porphyrazine systems was demonstrated. A range of selectively protected monosaccharide precursors was coupled to a small variety of phthalonitriles, the intermediates were co-macrocyclised to form hybrid porphyrazines in Linstead macrocyclisation reactions Demetallisation of Mg-porphyrazine products was readily effected to afford the free-base pigments, which were subsequently converted into their zinc or nickel complexes Some porphyrazines were deprotected of their isopropylidene groups (on the carbohydrate moieties) under acidic conditions to reveal polar OH groups The extraction coefficients of the porphyrazines between 2-octanol and phosphate buffered saline solution were measured. Comparison of the partition coefficients of the carbohydrate-substituted porphyrazines and their deprotected counterparts revealed that structural alteration offers a way to significantly increase the hydrophilicity of substituted porphyrazines (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2010.05.002
• 作为产物：
  描述：

  在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以90%的产率得到(2R,3S,4S,5R,6R)-2-((benzyloxy)methyl)-6-(((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate
  参考文献：
  名称：

  The synthesis and characterisation of carbohydrate-functionalised porphyrazines

  摘要：

  A synthetic pathway to the incorporation of mono- and disaccharide carbohydrate moieties into porphyrazine systems was demonstrated. A range of selectively protected monosaccharide precursors was coupled to a small variety of phthalonitriles, the intermediates were co-macrocyclised to form hybrid porphyrazines in Linstead macrocyclisation reactions Demetallisation of Mg-porphyrazine products was readily effected to afford the free-base pigments, which were subsequently converted into their zinc or nickel complexes Some porphyrazines were deprotected of their isopropylidene groups (on the carbohydrate moieties) under acidic conditions to reveal polar OH groups The extraction coefficients of the porphyrazines between 2-octanol and phosphate buffered saline solution were measured. Comparison of the partition coefficients of the carbohydrate-substituted porphyrazines and their deprotected counterparts revealed that structural alteration offers a way to significantly increase the hydrophilicity of substituted porphyrazines (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2010.05.002