breynin A | 50863-74-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: breynin A
• 英文别名: [(2S,3aR,4S,4'S,5'R,5aR,6R,8aS,8bS)-6-[(2S,3R,4S,5S,6R)-3-[(2S,3R,4S,5R,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3a,4-dihydroxy-5'-methyl-3-oxospiro[5,5a,6,7,8a,8b-hexahydro-4H-thieno[3,2-g][1]benzofuran-2,2'-oxane]-4'-yl] 4-hydroxybenzoate
• CAS: 50863-74-6
• 化学式: C₄₀H₅₆O₂₃S
• 分子量: 936.937
• InChiKey: VSMSZNRYCVGEDE-JYLRGUBCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.7
• 重原子数：
  64
• 可旋转键数：
  11
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  385
• 氢给体数：
  12
• 氢受体数：
  24

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 breynin A 以 甲醇 、 乙醚 为溶剂， 以60%的产率得到
  参考文献：
  名称：

  Structures of breynins A and B, architecturally complex orally active, hypocholesterolemic spiroketal glycosides

  摘要：

  Breynin A and its oxy congener, breynin B, were reisolated from the woody portion of the Taiwanese shrub Breynia officinalis Hemsl and formulated as 1 and 2, respectively. An arsenal of NMR techniques including DEPT, heteronuclear chemical shift correlation, H-1-H-1 COSY, and inverse long-range H-1-C-13 experiments were employed. Of particular importance for the NMR study was the preparation of breynin A undecaacetate (11). The analysis independently generated structure 1, confirming the assignment for breynin A recently reported by Ohkuma et al. However, spectral data and direct oxidation of breynin A to B demonstrated that the latter is not the hemithioacetal 8 as suggested by Ohkuma, but rather the isomeric sulfoxide 2. Improved purification of the Breynia glycosides via droplet counter-current distribution and HPLC is also described.

  DOI：

  10.1021/jo00045a022

文献信息

• Structures of breynins A and B, architecturally complex, hypocholesterolemic spiroketal glycosides. A revised formulation of breynin B
  作者：Amos B. Smith、Rex T. Gallagher、Terence P. Keenan、George T. Furst、Peter G. Dormer

  DOI：10.1016/0040-4039(91)80422-3

  日期：1991.11

  The complete structures of breynins A and B (1 and 2), orally active hypocholesterolemic glycosides, have been established via NMR analysis and chemical correlation. Breynin B (2) proved to be a sulfoxide derivative of 1, not the isomeric hemithioacetal 3 as proposed previously.

  通过NMR分析和化学相关性已经建立了布雷宁A和B（1和2）的完整结构，即口服活性降胆固醇的糖苷。Breynin B（2）被证明是的亚砜衍生物1，不同分异构的硫代半缩醛3如先前所提出的。