(2S,3R,4R,5S,6R)-6-((benzoyloxy)methyl)-2-methoxy-5-(tosyloxy)tetrahydro-2H-pyran-3,4-diyl dibenzoate | 74593-33-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3R,4R,5S,6R)-6-((benzoyloxy)methyl)-2-methoxy-5-(tosyloxy)tetrahydro-2H-pyran-3,4-diyl dibenzoate
• CAS: 74593-33-2
• 化学式: C₃₅H₃₂O₁₁S
• 分子量: 660.698
• InChiKey: FHLNEBIYPXODND-UEBWFRDWSA-N

物化性质

• 沸点：
  766.4±60.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.75
• 重原子数：
  47.0
• 可旋转键数：
  11.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  140.73
• 氢给体数：
  0.0
• 氢受体数：
  11.0

反应信息

• 作为产物：
  描述：

  甲基-D-半乳糖苷-2,3,6-三苯甲酸酯 、 对甲苯磺酰氯 生成 (2S,3R,4R,5S,6R)-6-((benzoyloxy)methyl)-2-methoxy-5-(tosyloxy)tetrahydro-2H-pyran-3,4-diyl dibenzoate
  参考文献：
  名称：

  Synthesis of 4-deoxy-d-xylo-hexose and 4-azido-4-deoxy-d-glucose and their effects on lactose synthase

  摘要：

  Syntheses are reported of 4-deoxy-D-xylo-hexose and 4-azido-4-deoxy-D-glucose as potential inhibitors for lactose synthase [uridine 5'-(alpha-D-galactopyranosyl pyrophosphate):D-glucose 4-beta-D-galactopyranosyltransferase, EC 2.4.1.22]. These syntheses involved SN2 displacement of the 4-methylsulfonyloxy group of methyl 2,3,6-tri-O-benzoyl-4-O-methylsulfonyl-alpha-D-galactopyranoside by iodide and azide ions. In both cases, inversion in configuration was observed. The resulting intermediates, methyl 2,3,6-tri-O-benzoyl-4-deoxy-4-iodo-alpha-D-glucopyranoside and methyl 4-azido-2,3,6-tri-O-benzoyl-4-deoxy-alpha-D-glucopyranoside, were obtained in crystalline form. Both 4-deoxy-D-xylo-hexose and 4-azido-4-deoxy-D-glucose were found to be inhibitors for lactose synthase in the presence of alpha-lactalbumin, but had no effect in the absence of alpha-lactalbumin. Both D-glucose analogues bind to the enzyme system far more weakly than D-glucose, suggesting that the recognition of the 4-OH group of the acceptor substrate is an important factor in binding.

  DOI：

  10.1016/s0008-6215(00)85655-4