methyl 6-deoxy-6-[bis(benzyloxycarbonyl)methyl]-2,3,4-tri-O-benzyl-α-D-mannopyranoside | 833489-18-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 6-deoxy-6-[bis(benzyloxycarbonyl)methyl]-2,3,4-tri-O-benzyl-α-D-mannopyranoside
• CAS: 833489-18-2
• 化学式: C₄₅H₄₆O₉
• 分子量: 730.855
• InChiKey: HZCKGDXWQHLSTG-WFFVNDTGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.61
• 重原子数：
  54.0
• 可旋转键数：
  18.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  98.75
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  methyl 6-deoxy-6-[bis(benzyloxycarbonyl)methyl]-2,3,4-tri-O-benzyl-α-D-mannopyranoside 在 palladium dihydroxide 氢气 作用下， 以 乙酸乙酯 、 异丙醇 为溶剂， 以82%的产率得到methyl 6-deoxy-6-dicarboxymethyl-α-D-mannopyranoside bis(ammonium) salt
  参考文献：
  名称：

  Mono- and Bivalent Ligands Bearing Mannose 6-Phosphate (M6P) Surrogates:  Targeting the M6P/Insulin-Like Growth Factor II Receptor

  摘要：

  Mannose 6-phosphate mimics locked into the alpha-configuration and bearing hydrolase-resistant phosphate surrogates were synthesized and evaluated for binding affinity to the mannose 6-phosphate/insulin-like-growth factor II receptor (M6P/IGF2R). Affinity increases as the phosphate surrogate is varied in the order malonyl ether < malonate < phosphonate. An alkene cross-metathesis approach to sought-after bivalent M6P-bearing ligands is also described. These compounds were designed to map onto biantennary sectors of high-mannose-type oligosaccharides carried by glycoprotein M6P/IGF2R ligands.

  DOI：

  10.1021/ol0479444
• 作为产物：
  描述：

  ((2R,3R,4S,5S,6S)-3,4,5-三(苄氧基)-6-甲氧基四氢-2H-吡喃-2-基)甲醇 在 2,6-二叔丁基-4-甲基吡啶 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 8.0h， 生成 methyl 6-deoxy-6-[bis(benzyloxycarbonyl)methyl]-2,3,4-tri-O-benzyl-α-D-mannopyranoside
  参考文献：
  名称：

  Mono- and Bivalent Ligands Bearing Mannose 6-Phosphate (M6P) Surrogates:  Targeting the M6P/Insulin-Like Growth Factor II Receptor

  摘要：

  Mannose 6-phosphate mimics locked into the alpha-configuration and bearing hydrolase-resistant phosphate surrogates were synthesized and evaluated for binding affinity to the mannose 6-phosphate/insulin-like-growth factor II receptor (M6P/IGF2R). Affinity increases as the phosphate surrogate is varied in the order malonyl ether < malonate < phosphonate. An alkene cross-metathesis approach to sought-after bivalent M6P-bearing ligands is also described. These compounds were designed to map onto biantennary sectors of high-mannose-type oligosaccharides carried by glycoprotein M6P/IGF2R ligands.

  DOI：

  10.1021/ol0479444