broussonetine F | 190317-57-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: broussonetine F
• 英文别名: (R)-13-((2R,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)pyrrolidin-2-yl)-1,13-dihydroxytridecan-5-one；(13R)-13-[(2R,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)pyrrolidin-2-yl]-1,13-dihydroxytridecan-5-one
• CAS: 190317-57-8
• 化学式: C₁₈H₃₅NO₆
• 分子量: 361.479
• InChiKey: OPUBENBDVFCFOI-DUQPFJRNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  25
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  130
• 氢给体数：
  6
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  broussonetine F 在 吡啶 、 碳酸氢钠 作用下， 以 四氢呋喃 为溶剂， 反应 72.0h， 生成 [(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：

  在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以73%的产率得到broussonetine F
  参考文献：
  名称：

  Broussonetine F的全合成：烯丙二酚的原酰胺超量重排

  摘要：

  由1-酒石酸二乙酯实现了布鲁索汀F的第一全合成。我们合成的基石是原酰胺Overman重排，可提供具有完全非对映选择性的烯丙基氨基醇。

  DOI：

  10.1021/ol102856j

文献信息

• Total Synthesis of Broussonetine F: The Orthoamide Overman Rearrangement of an Allylic Diol
  作者：Naoto Hama、Toshihiro Aoki、Shohei Miwa、Miki Yamazaki、Takaaki Sato、Noritaka Chida

  DOI：10.1021/ol102856j

  日期：2011.2.18

  A first total synthesis of broussonetine F from diethyl l-tartrate was achieved. The cornerstone of our synthesis was an orthoamide Overman rearrangement, which provided an allylic amino alcohol with complete diastereoselectivity.

  由1-酒石酸二乙酯实现了布鲁索汀F的第一全合成。我们合成的基石是原酰胺Overman重排，可提供具有完全非对映选择性的烯丙基氨基醇。
• Studies on the Constituents of Broussonetia Species. V. Two New Pyrrolidine Alkaloids, Broussonetines K and L, as Inhibitors of Glycosidase, from Broussonetia kazinoki SIEB.
  作者：Makio SHIBANO、Satoko NAKAMURA、Naomi MOTOYA、Genjiro KUSANO

  DOI：10.1248/cpb.47.472

  日期：——

  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.