(2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(4-(4-(prop-2-yn-1-yloxy)benzoyl)phenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate | 1208396-02-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(4-(4-(prop-2-yn-1-yloxy)benzoyl)phenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate
• CAS: 1208396-02-4
• 化学式: C₃₀H₃₀O₁₂
• 分子量: 582.561
• InChiKey: DWKVSAULZASJKP-LXRLAABLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.39
• 重原子数：
  42.0
• 可旋转键数：
  11.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  149.96
• 氢给体数：
  0.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(4-(4-(prop-2-yn-1-yloxy)benzoyl)phenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate 在 甲醇 、 sodium methylate 作用下， 反应 0.5h， 生成 (4-prop-2-ynoxyphenyl)-[4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]methanone
  参考文献：
  名称：

  Nanomolar affinity, iminosugar-based chemical probes for specific labeling of lysosomal glucocerebrosidase

  摘要：

  Three different photoprobes were synthesized to label beta-glucosidases; one probe was based on glucose, two probes on the iminosugar deoxynojirimycin. The affinity of the probes for three different beta-glucosidases was determined. Furthermore, their labeling efficiencies, binding specificities through competition with deoxynojirimycin, and binding specificities in the presence of cell lysate, were evaluated. Especially one showed very high affinity towards non-lysosomal glucoceramidase (IC50 = 20 nM). (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.10.060
• 作为产物：
  描述：

  (4-hydroxyphenyl)(4-(prop-2-yn-1-yloxy)phenyl)methanone 、 2,3,4,6-四邻乙酰基-alpha-d-吡喃葡萄糖三氯乙酰胺 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以41 mg的产率得到(2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(4-(4-(prop-2-yn-1-yloxy)benzoyl)phenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate
  参考文献：
  名称：

  Nanomolar affinity, iminosugar-based chemical probes for specific labeling of lysosomal glucocerebrosidase

  摘要：

  Three different photoprobes were synthesized to label beta-glucosidases; one probe was based on glucose, two probes on the iminosugar deoxynojirimycin. The affinity of the probes for three different beta-glucosidases was determined. Furthermore, their labeling efficiencies, binding specificities through competition with deoxynojirimycin, and binding specificities in the presence of cell lysate, were evaluated. Especially one showed very high affinity towards non-lysosomal glucoceramidase (IC50 = 20 nM). (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.10.060