Breynin A dodecaacetate | 142895-92-9

• 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 dodecaacetate
• 英文别名: [(2S,3aR,4S,4'S,5'R,5aR,6R,8aS,8bS)-3a,4-diacetyloxy-6-[(2S,3R,4S,5R,6R)-4,5-diacetyloxy-6-(acetyloxymethyl)-3-[(2S,3R,4S,5R,6R)-3,5-diacetyloxy-6-(acetyloxymethyl)-4-[(2S,3R,4R,5S,6S)-3,4,5-triacetyloxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxyoxan-2-yl]oxy-5'-methyl-3-oxospiro[5,5a,6,7,8a,8b-hexahydro-4H-thieno[3,2-g][1]benzofuran-2,2'-oxane]-4'-yl] 4-acetyloxybenzoate
• CAS: 142895-92-9
• 化学式: C₆₄H₈₀O₃₅S
• 分子量: 1441.38
• InChiKey: WZUDTPQLUSQIGN-MKNKTNBESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  100
• 可旋转键数：
  35
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  458
• 氢给体数：
  0
• 氢受体数：
  36

反应信息

• 作为产物：
  描述：

  乙酸酐 、 breynin A 在 吡啶 、 4-二甲氨基吡啶 作用下， 反应 48.0h， 以7%的产率得到Breynin A dodecaacetate
  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