Breynin A undecaacetate | 139299-94-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Breynin A undecaacetate
• CAS: 139299-94-8
• 化学式: C₆₂H₇₈O₃₄S
• 分子量: 1399.35
• InChiKey: FTDZWFVECZMDBY-QTYMUOQMSA-N

反应信息

• 作为产物：
  描述：

  乙酸酐 、 breynin A 在 4-二甲氨基吡啶 吡啶 作用下， 生成 Breynin A undecaacetate
  参考文献：
  名称：

  breynins A和B的结构，结构复杂，降胆固醇的螺酮糖苷。Breynin B的修订配方

  摘要：

  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。

  DOI：

  10.1016/0040-4039(91)80422-3

文献信息

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

  DOI：10.1021/jo00045a022

  日期：1992.9

  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.