methyl 6-deoxy-6-(dibenzyl)phosphonomethyl-2,3,4-tri-O-benzyl-α-D-mannopyranoside | 221545-53-5

• 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-(dibenzyl)phosphonomethyl-2,3,4-tri-O-benzyl-α-D-mannopyranoside
• 英文别名: (2R,3R,4S,5S,6S)-2-[2-bis(phenylmethoxy)phosphorylethyl]-6-methoxy-3,4,5-tris(phenylmethoxy)oxane
• CAS: 221545-53-5
• 化学式: C₄₃H₄₇O₈P
• 分子量: 722.815
• InChiKey: QTMAHEAQQSMAOX-FYYRRIAOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.13
• 重原子数：
  52.0
• 可旋转键数：
  19.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  81.68
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  methyl 6-deoxy-6-(dibenzyl)phosphonomethyl-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78%的产率得到methyl 6-deoxy-6-phosphonomethyl-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：

  sodium dibenzyl phosphite 在 六甲基磷酰三胺 、 正丁基锂 作用下， 反应 0.42h， 生成 methyl 6-deoxy-6-(dibenzyl)phosphonomethyl-2,3,4-tri-O-benzyl-α-D-mannopyranoside
  参考文献：
  名称：

  Facile installation of the phosphonate and (α,α-difluoromethyl)phosphonate functionalities equipped with benzyl protection

  摘要：

  Under appropriate conditions, dibenzyl (lithiomethyl)phosphonate and dibenzyl (lithiodifluoromethyl)phosphonate displace primary triflates to provide convenient access to the corresponding phosphonates, carrying benzyl ester protecting groups. This approach is of particular advantage for phosphonate ester deprotection, which may be achieved by simple hydrogenolysis. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00077-5