(2R,3R,4S,5R,6S)-2-(((2R,3R,4S,5R,6S)-4,5-bis(benzoyloxy)-2-((benzoyloxy)methyl)-6-phenoxytetrahydro-2H-pyran-3-yl)oxy)-6-(bromomethyl)tetrahydro-2H-pyran-3,4,5-triyl tribenzoate | 847237-43-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2R,3R,4S,5R,6S)-2-(((2R,3R,4S,5R,6S)-4,5-bis(benzoyloxy)-2-((benzoyloxy)methyl)-6-phenoxytetrahydro-2H-pyran-3-yl)oxy)-6-(bromomethyl)tetrahydro-2H-pyran-3,4,5-triyl tribenzoate
• CAS: 847237-43-8
• 化学式: C₆₀H₄₉BrO₁₆
• 分子量: 1105.94
• InChiKey: NSEXJDHLFBXIBG-SWKRGCDQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.28
• 重原子数：
  77.0
• 可旋转键数：
  18.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  194.72
• 氢给体数：
  0.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  (2R,3R,4S,5R,6S)-2-(((2R,3R,4S,5R,6S)-4,5-bis(benzoyloxy)-2-((benzoyloxy)methyl)-6-phenoxytetrahydro-2H-pyran-3-yl)oxy)-6-(bromomethyl)tetrahydro-2H-pyran-3,4,5-triyl tribenzoate 在 palladium on activated charcoal 4 A molecular sieve 、 氢气 、 sodium methylate 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 48.5h， 生成 phenyl 4-O-(6-deoxy-β-D-galactopyranosyl)-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of deoxy and acylamino derivatives of lactose and use of these for probing the active site of Neisseria meningitidis N-acetylglucosaminyltransferase

  摘要：

  Derivatives of lactose with the galactose ring substituents replaced by deoxy or acylamino functions were prepared. The 2'-, 3'-. 4'- and 6'-deoxy, 3'-acetamido and 3'-benzamido derivatives of phenyl 4-O-(beta-D-galactopyranosyl)-beta-D-glucopyranoside (phenyl P-lactoside) were synthesized from disaccharide or monosaccharide precursors. The derivatives were tested as substrates for the N-acetylglucosaminyltransferase from Neisseria meningitidis, which uses lactosyl derivatives as acceptors and UDP-GlcNAc as the donor in a beta-(1-->3) glycosylation reaction. The 6'-deoxy derivative was nearly threefold as active as phenyl beta-lactoside, whereas the 2'- and 4'-deoxy derivatives were less active. The other derivatives were inactive, as expected. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2004.11.017
• 作为产物：
  描述：

  1',2',3',6',2,3,4,6-octa-O-acetyl-β-D-lactose 在 N-溴代丁二酰亚胺(NBS) 、 4 A molecular sieve 、 三氟化硼乙醚 、 sodium methylate 、 对甲苯磺酸 、 barium carbonate 作用下， 以 吡啶 、 甲醇 、 四氯化碳 、 二氯甲烷 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 20.0~85.0 ℃ 、20.0 kPa 条件下， 反应 12.0h， 生成 (2R,3R,4S,5R,6S)-2-(((2R,3R,4S,5R,6S)-4,5-bis(benzoyloxy)-2-((benzoyloxy)methyl)-6-phenoxytetrahydro-2H-pyran-3-yl)oxy)-6-(bromomethyl)tetrahydro-2H-pyran-3,4,5-triyl tribenzoate
  参考文献：
  名称：

  Synthesis of deoxy and acylamino derivatives of lactose and use of these for probing the active site of Neisseria meningitidis N-acetylglucosaminyltransferase

  摘要：

  Derivatives of lactose with the galactose ring substituents replaced by deoxy or acylamino functions were prepared. The 2'-, 3'-. 4'- and 6'-deoxy, 3'-acetamido and 3'-benzamido derivatives of phenyl 4-O-(beta-D-galactopyranosyl)-beta-D-glucopyranoside (phenyl P-lactoside) were synthesized from disaccharide or monosaccharide precursors. The derivatives were tested as substrates for the N-acetylglucosaminyltransferase from Neisseria meningitidis, which uses lactosyl derivatives as acceptors and UDP-GlcNAc as the donor in a beta-(1-->3) glycosylation reaction. The 6'-deoxy derivative was nearly threefold as active as phenyl beta-lactoside, whereas the 2'- and 4'-deoxy derivatives were less active. The other derivatives were inactive, as expected. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2004.11.017