(5R,6R,7R,7aR)-5-((S)-10,13-Dihydroxy-tridecyl)-6,7-dihydroxy-tetrahydro-pyrrolo[1,2-c]oxazol-3-one | 304678-31-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (5R,6R,7R,7aR)-5-((S)-10,13-Dihydroxy-tridecyl)-6,7-dihydroxy-tetrahydro-pyrrolo[1,2-c]oxazol-3-one
• 英文别名: (5R,6R,7R,7aR)-5-[(10S)-10,13-dihydroxytridecyl]-6,7-dihydroxy-5,6,7,7a-tetrahydro-1H-pyrrolo[1,2-c][1,3]oxazol-3-one
• CAS: 304678-31-7
• 化学式: C₁₉H₃₅NO₆
• 分子量: 373.49
• InChiKey: RBVHZHOZNXNEGI-YYWYGQEZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  26
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  111
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (R)-methoxytrifluoromethylphenylacetyl chloride 、 (5R,6R,7R,7aR)-5-((S)-10,13-Dihydroxy-tridecyl)-6,7-dihydroxy-tetrahydro-pyrrolo[1,2-c]oxazol-3-one 在 吡啶 作用下， 以1.5 mg的产率得到[(4S)-13-[(5R,6R,7R,7aR)-3-oxo-6,7-bis[[(2S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoyl]oxy]-5,6,7,7a-tetrahydro-1H-pyrrolo[1,2-c][1,3]oxazol-5-yl]-4-[(2S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoyl]oxytridecyl] (2S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoate
  参考文献：
  名称：

  Studies on the Constituents of Broussonetia Species. VII. Four New Pyrrolidine Alkaloids, Broussonetines M, O, P, and Q, as Inhibitors of Glycosidase, from Broussonetia kazinoki SIEB.

  摘要：

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

  DOI：

  10.1248/cpb.48.1281
• 作为产物：
  描述：

  氯甲酸苯酯 、 broussonetine M 在 碳酸氢钠 作用下， 以 四氢呋喃 为溶剂， 反应 38.0h， 以8 mg的产率得到(5R,6R,7R,7aR)-5-((S)-10,13-Dihydroxy-tridecyl)-6,7-dihydroxy-tetrahydro-pyrrolo[1,2-c]oxazol-3-one
  参考文献：
  名称：

  Studies on the Constituents of Broussonetia Species. VII. Four New Pyrrolidine Alkaloids, Broussonetines M, O, P, and Q, as Inhibitors of Glycosidase, from Broussonetia kazinoki SIEB.

  摘要：

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

  DOI：

  10.1248/cpb.48.1281