grayanotoxins V

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: grayanotoxins V
• 英文别名: Grayanotoxin V；(1S,3R,4R,8S,9R,10R,13R,14R,16R)-3,4,9,14,16-pentahydroxy-5,5,9,14-tetramethyltetracyclo[11.2.1.01,10.04,8]hexadecan-6-one
• 化学式: C₂₀H₃₂O₆
• 分子量: 368.47
• InChiKey: DSVGYNOFYJLKLN-KJUYHJNSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  26
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  118
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  5,6:14,16-O-Diethyliden-3-dehydro-G III 生成 grayanotoxins V
  参考文献：
  名称：

  Conversion of grayanotoxin III to grayanotoxin V, rhodojaponin III and rhodojaponin IV.

  摘要：

  Treatment of grayanotoxin (G) III with CH3CHO in the presence of anhydrous CuSO4 afforded a diethylidene compound (2). Oxidation of 2 (CrO3) and subsequent ozonolysis and hydrolysis (KOH-MeOH) gave G-V (4) in 34% overall yield. Direct ozonolysis of 2 produced rhodojaponin (R) IV (8) in 68% yield. Δ2-Diethylidene compoud (10) was oxidized to 11, which on ozonolysis-hydrolysis furnished R-III (12) in 9.2% overall yield.

  DOI：

  10.1248/cpb.26.1615

文献信息

• Conversion of grayanotoxin III to grayanotoxin V, rhodojaponin III and rhodojaponin IV.
  作者：TADAMASA TERAI、MASAAKI KATAI、NOBUYUKI HAMANAKA、TAKESHI MATSUMOTO、HARUO MEGURI

  DOI：10.1248/cpb.26.1615

  日期：——

  Treatment of grayanotoxin (G) III with CH3CHO in the presence of anhydrous CuSO4 afforded a diethylidene compound (2). Oxidation of 2 (CrO3) and subsequent ozonolysis and hydrolysis (KOH-MeOH) gave G-V (4) in 34% overall yield. Direct ozonolysis of 2 produced rhodojaponin (R) IV (8) in 68% yield. Δ2-Diethylidene compoud (10) was oxidized to 11, which on ozonolysis-hydrolysis furnished R-III (12) in 9.2% overall yield.