L-menthyl (S)-(2E,6E,8E)-5-hydroxy-6-methyl-2,6,8-heptadecatrienoate | 1238375-27-3

• 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: L-menthyl (S)-(2E,6E,8E)-5-hydroxy-6-methyl-2,6,8-heptadecatrienoate
• CAS: 1238375-27-3
• 化学式: C₂₈H₄₈O₃
• 分子量: 432.687
• InChiKey: FPVCWHJXXPMGKH-URYYPVKKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.55
• 重原子数：
  31.0
• 可旋转键数：
  14.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  (2E,4E)-2-methyl-2,4-tridecadienal 、 1-(1'R,2'S,5'R)-5'-methyl-2'-(1-methylethyl)cyclohexoxy-1-(tert-butyldimethylsiloxy)-1,3-butadiene 在 N,N′-双[(11BR)-3,5-二氢-3,5-二甲基-4-环氧-4H-二萘并[2,1-D:1′,2′-F][1,3,2]二氮杂磷杂庚英-4-基]-N,N′-二甲基-1,5-戊二胺 、 四氯化硅 、 N,N-二异丙基乙胺 、 potassium fluoride 、 potassium dihydrogenphosphate 、 水 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 生成 L-menthyl (S)-(2E,6E,8E)-5-hydroxy-6-methyl-2,6,8-heptadecatrienoate 、 L-menthyl (R)-(2E,6E,8E)-5-hydroxy-6-methyl-2,6,8-heptadecatrienoate
  参考文献：
  名称：

  Total synthesis of (+)-papulacandin D

  摘要：

  A total synthesis of (+)-papulacandin D has been achieved in 31 steps, in a 9.2% overall yield from commercially available materials. The synthetic strategy divided the molecule into two nearly equal sized subunits, the spirocyclic C-arylglycopyranoside and the polyunsaturated fatty acid side-chain. The C-arylglycopyranoside was prepared in 11 steps in a 30% overall yield from triacetoxyglucal. The fatty acid side-chain was also prepared in 11 steps in a 30% overall yield from geraniol. The key strategic transformations in the synthesis are: (1) a palladium-catalyzed, organosilanolate-based cross-coupling reaction of a dimethylglucal-silanol with an electron-rich and sterically hindered aromatic iodide and (2) a Lewis-base catalyzed, enantioselective allylation reaction of a dienal and allyltrichlorosilane. A critical element in the successful execution of the synthesis was the development of a suitable protecting group strategy that satisfied a number of stringent criteria. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.03.093