allyl 6-deoxy-6-[bis(benzyloxycarbonyl)methyl]-2,3,4-tri-O-benzyl-α-D-mannopyranoside | 833489-23-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: allyl 6-deoxy-6-[bis(benzyloxycarbonyl)methyl]-2,3,4-tri-O-benzyl-α-D-mannopyranoside
• CAS: 833489-23-9
• 化学式: C₄₇H₄₈O₉
• 分子量: 756.893
• InChiKey: AGXFMVAOFYJSPA-FEHBFAEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.16
• 重原子数：
  56.0
• 可旋转键数：
  20.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.28
• 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：

  allyl 6-deoxy-6-[bis(benzyloxycarbonyl)methyl]-2,3,4-tri-O-benzyl-α-D-mannopyranoside 在 Grubbs catalyst first generation 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 生成 2-Benzyloxycarbonyl-3-((2R,3R,4S,5S,6S)-3,4,5-tris-benzyloxy-6-{(Z)-4-[(2S,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-(2,2-bis-benzyloxycarbonyl-ethyl)-tetrahydro-pyran-2-yloxy]-but-2-enyloxy}-tetrahydro-pyran-2-yl)-propionic acid benzyl ester 、 2-Benzyloxycarbonyl-3-((2R,3R,4S,5S,6S)-3,4,5-tris-benzyloxy-6-{(E)-4-[(2S,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-(2,2-bis-benzyloxycarbonyl-ethyl)-tetrahydro-pyran-2-yloxy]-but-2-enyloxy}-tetrahydro-pyran-2-yl)-propionic acid benzyl ester
  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：

  allyl 2,3,4-tri-O-benzyl-α-D-mannopyranoside 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 2.5h， 生成 allyl 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