(2R,3R,4S,5R,6R)-6-((benzoyloxy)methyl)-5-(((4aR,6S,7R,8S,8aS)-7,8-bis(benzoyloxy)-2-(naphthalen-2-yl)hexahydropyrano[3,2-d][1,3]dioxin-6-yl)oxy)-2-(pent-4-en-1-yloxy)tetrahydro-2H-pyran-3,4-diyl dibenzoate | 161767-01-7

• 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,6R)-6-((benzoyloxy)methyl)-5-(((4aR,6S,7R,8S,8aS)-7,8-bis(benzoyloxy)-2-(naphthalen-2-yl)hexahydropyrano[3,2-d][1,3]dioxin-6-yl)oxy)-2-(pent-4-en-1-yloxy)tetrahydro-2H-pyran-3,4-diyl dibenzoate
• CAS: 161767-01-7
• 化学式: C₆₃H₅₆O₁₆
• 分子量: 1069.13
• InChiKey: CIHSUNUUCFMFLU-HNBQSYKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.83
• 重原子数：
  79.0
• 可旋转键数：
  19.0
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  186.88
• 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,6R)-6-((benzoyloxy)methyl)-5-(((4aR,6S,7R,8S,8aS)-7,8-bis(benzoyloxy)-2-(naphthalen-2-yl)hexahydropyrano[3,2-d][1,3]dioxin-6-yl)oxy)-2-(pent-4-en-1-yloxy)tetrahydro-2H-pyran-3,4-diyl dibenzoate 在 三氯化铝 、 硼烷-三甲胺络合物 、 4 A molecular sieve 、 sodium methylate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 64.0h， 生成 n-pentenyl <6-O-(2-naphthylmethyl)-β-D-galactopyranosyl>-(1<*>4)-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of bi-fluorescence-labeled lactoside: A substrate for continual assay of ceramide glycanase

  摘要：

  A bi-fluorescence labeled derivative suitable for analysis of ceramide glycanase activity was constructed from 4-pentenyl lactoside. Selective modification of the galactosyl residue was attained by formation of 4',6'-naphthylmethylidene derivative, which was followed by regioselective reductive ring opening. The aglycon was extended by Michael addition of 2-aminoethanetiol, and dansylated at the terminal amino group. Excitation of the naphthyl group results in emission from the dansyl group, while the emission from the naphthyl group is quenched by the dansyl group. Upon digestion with ceramide glycanase, the energy transfer is severed and a decrease in the dansyl emission concommitant with an increase in the naphthyl emission was observed. This substrate was successfully used to analyze ceramide glycanase activity.

  DOI：

  10.1016/s0957-4166(00)80383-3
• 作为产物：
  描述：

  4-pentenyl 4-O-β-D-galactopyranosyl-β-D-glucopyranoside 在 吡啶 、 D(+)-10-樟脑磺酸 作用下， 反应 5.0h， 生成 (2R,3R,4S,5R,6R)-6-((benzoyloxy)methyl)-5-(((4aR,6S,7R,8S,8aS)-7,8-bis(benzoyloxy)-2-(naphthalen-2-yl)hexahydropyrano[3,2-d][1,3]dioxin-6-yl)oxy)-2-(pent-4-en-1-yloxy)tetrahydro-2H-pyran-3,4-diyl dibenzoate
  参考文献：
  名称：

  Synthesis of bi-fluorescence-labeled lactoside: A substrate for continual assay of ceramide glycanase

  摘要：

  A bi-fluorescence labeled derivative suitable for analysis of ceramide glycanase activity was constructed from 4-pentenyl lactoside. Selective modification of the galactosyl residue was attained by formation of 4',6'-naphthylmethylidene derivative, which was followed by regioselective reductive ring opening. The aglycon was extended by Michael addition of 2-aminoethanetiol, and dansylated at the terminal amino group. Excitation of the naphthyl group results in emission from the dansyl group, while the emission from the naphthyl group is quenched by the dansyl group. Upon digestion with ceramide glycanase, the energy transfer is severed and a decrease in the dansyl emission concommitant with an increase in the naphthyl emission was observed. This substrate was successfully used to analyze ceramide glycanase activity.

  DOI：

  10.1016/s0957-4166(00)80383-3