Trifluoro-methanesulfonic acid (2R,3R,4S,5S,6S)-3,4,5-tris-benzyloxy-6-[(E)-4-((2S,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-trifluoromethanesulfonyloxymethyl-tetrahydro-pyran-2-yloxy)-but-2-enyloxy]-tetrahydro-pyran-2-ylmethyl ester | 833489-27-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Trifluoro-methanesulfonic acid (2R,3R,4S,5S,6S)-3,4,5-tris-benzyloxy-6-[(E)-4-((2S,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-trifluoromethanesulfonyloxymethyl-tetrahydro-pyran-2-yloxy)-but-2-enyloxy]-tetrahydro-pyran-2-ylmethyl ester
• CAS: 833489-27-3
• 化学式: C₆₀H₆₂F₆O₁₆S₂
• 分子量: 1217.27
• InChiKey: BTOMFHIPHZNSQN-PHPFIDIWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.27
• 重原子数：
  84.0
• 可旋转键数：
  30.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  179.04
• 氢给体数：
  0.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  Trifluoro-methanesulfonic acid (2R,3R,4S,5S,6S)-3,4,5-tris-benzyloxy-6-[(E)-4-((2S,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-trifluoromethanesulfonyloxymethyl-tetrahydro-pyran-2-yloxy)-but-2-enyloxy]-tetrahydro-pyran-2-ylmethyl ester 、 膦酸,甲基-,二(苯基甲基)酯 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.5h， 以75%的产率得到{2-[(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-(bis-benzyloxy-phosphoryl)-ethyl]-tetrahydro-pyran-2-yloxy}-but-2-enyloxy)-tetrahydro-pyran-2-yl]-ethyl}-phosphonic acid dibenzyl 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 Grubbs catalyst first generation 2,6-二叔丁基-4-甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 10.5h， 生成 Trifluoro-methanesulfonic acid (2R,3R,4S,5S,6S)-3,4,5-tris-benzyloxy-6-[(E)-4-((2S,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-trifluoromethanesulfonyloxymethyl-tetrahydro-pyran-2-yloxy)-but-2-enyloxy]-tetrahydro-pyran-2-ylmethyl 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