Acetic acid (R)-13-acetoxy-1-((5S,6R,7R,7aR)-6,7-dihydroxy-3-oxo-tetrahydro-pyrrolo[1,2-c]oxazol-5-yl)-9-oxo-tridecyl ester | 229467-81-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯里西啶类
• 英文名称: Acetic acid (R)-13-acetoxy-1-((5S,6R,7R,7aR)-6,7-dihydroxy-3-oxo-tetrahydro-pyrrolo[1,2-c]oxazol-5-yl)-9-oxo-tridecyl ester
• 英文别名: [(13R)-13-acetyloxy-13-[(5S,6R,7R,7aR)-6,7-dihydroxy-3-oxo-5,6,7,7a-tetrahydro-1H-pyrrolo[1,2-c][1,3]oxazol-5-yl]-5-oxotridecyl] acetate
• CAS: 229467-81-6
• 化学式: C₂₃H₃₇NO₉
• 分子量: 471.548
• InChiKey: ZJVHUCSBGWRIDS-ZGJYDULXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  33
• 可旋转键数：
  17
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  140
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  苯甲酰氯 、 Acetic acid (R)-13-acetoxy-1-((5S,6R,7R,7aR)-6,7-dihydroxy-3-oxo-tetrahydro-pyrrolo[1,2-c]oxazol-5-yl)-9-oxo-tridecyl ester 在 吡啶 作用下， 反应 36.0h， 以6.5 mg的产率得到[(5R,6R,7R,7aR)-6-benzoyloxy-5-[(1R)-1,13-diacetyloxy-9-oxotridecyl]-3-oxo-5,6,7,7a-tetrahydro-1H-pyrrolo[1,2-c][1,3]oxazol-7-yl] benzoate
  参考文献：
  名称：

  Studies on the Constituents of Broussonetia Species. V. Two New Pyrrolidine Alkaloids, Broussonetines K and L, as Inhibitors of Glycosidase, from Broussonetia kazinoki SIEB.

  摘要：

  Two new pyrrolidine alkaloids, broussonetines K and L, were isolated from the branches of Broussonetia kazinoki SIEB. (Moraceae). Broussonetines K and L were formulated as (2R, 3R, 4R, 5R)-2-hydroxymethyl-3, 4-dihydroxy-5-[(1R)-1-hydroxy-10-oxo-13-(β-D-glucopyranosyloxy) tridecyl] pyrrolidine (1) and (2R, 3R, 4R, 5R)-2-hydroxymethyl-3, 4-dihydroxy-5-[(1R)-1-hydroxy-9-oxo-13-(β-D-glucopyranosyloxy) tridecyl] pyrrolidine (2), respectively, by spectroscopic and chemical methods. 1 and 2 inhibited β-glucosidase, β-galactosidase and β-mannosidase.

  DOI：

  10.1248/cpb.47.472
• 作为产物：
  描述：

  broussonetine F 在 吡啶 、 碳酸氢钠 作用下， 以 四氢呋喃 为溶剂， 反应 36.0h， 生成 Acetic acid (R)-13-acetoxy-1-((5S,6R,7R,7aR)-6,7-dihydroxy-3-oxo-tetrahydro-pyrrolo[1,2-c]oxazol-5-yl)-9-oxo-tridecyl ester
  参考文献：
  名称：

  Studies on the Constituents of Broussonetia Species. V. Two New Pyrrolidine Alkaloids, Broussonetines K and L, as Inhibitors of Glycosidase, from Broussonetia kazinoki SIEB.

  摘要：

  Two new pyrrolidine alkaloids, broussonetines K and L, were isolated from the branches of Broussonetia kazinoki SIEB. (Moraceae). Broussonetines K and L were formulated as (2R, 3R, 4R, 5R)-2-hydroxymethyl-3, 4-dihydroxy-5-[(1R)-1-hydroxy-10-oxo-13-(β-D-glucopyranosyloxy) tridecyl] pyrrolidine (1) and (2R, 3R, 4R, 5R)-2-hydroxymethyl-3, 4-dihydroxy-5-[(1R)-1-hydroxy-9-oxo-13-(β-D-glucopyranosyloxy) tridecyl] pyrrolidine (2), respectively, by spectroscopic and chemical methods. 1 and 2 inhibited β-glucosidase, β-galactosidase and β-mannosidase.

  DOI：

  10.1248/cpb.47.472