6-Thia-4,8,13,17,21-pentamethyl-4(E),8(E),12(E),16(E),20-docosapentaenyl tert-butyldimethylsilyl ether | 158897-36-0

• 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: 6-Thia-4,8,13,17,21-pentamethyl-4(E),8(E),12(E),16(E),20-docosapentaenyl tert-butyldimethylsilyl ether
• 英文别名: tert-butyl-dimethyl-[(E)-4-methyl-5-[(2E,6E,10E)-2,7,11,15-tetramethylhexadeca-2,6,10,14-tetraenyl]sulfanylpent-4-enoxy]silane
• CAS: 158897-36-0
• 化学式: C₃₂H₅₈OSSi
• 分子量: 518.963
• InChiKey: LYQSHRAABQRPHQ-NXGADILBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.57
• 重原子数：
  35
• 可旋转键数：
  18
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  34.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-Thia-4,8,13,17,21-pentamethyl-4(E),8(E),12(E),16(E),20-docosapentaenyl tert-butyldimethylsilyl ether 在 草酰氯 、 四丁基氟化铵 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 10.5h， 生成 6-Thia-4,8,13,17,21-pentamethyl-4(E),8(E),12(E),16(E),20-docosapentaen-1-al
  参考文献：
  名称：

  Synthesis of (6E)-8-Thia- and (14E)-13-Thia-2,3-oxidosqualene: Inhibitors of 2,3-Oxidosqualene-Lanosterol Cyclase

  摘要：

  Synthesis of (6E)-8-thia-2,3-oxidosqualene (22) and (14E)-13-thia-2,3-oxidosqualene (34) as inhibitors of 2,3-oxidosqualene-lanosterol cyclase are reported. Synthesis of 22 required the stereospecific generation of a vinyl sulfide. This was achieved by a new coupling of a benzenethiosulfonate (15) and a lithiated vinyl iodide (18). Synthesis of 34 involved similar coupling of benzenethiosulfonate 29 with lithium reagent obtained from vinyl iodide 33. The required (E)-vinyl iodides 18 and 33 were prepared by zirconium-catalyzed carboalumination of 4-pentyn-1-ol, (16) and 2,6-dimethyl-2(E),6(E)-dien-10-yne (32) respectively. Both 22 and 34 inhibited 2,3-oxidosqualene-lanosterol cyclase from Candida albicans with IC50 values of 0.68 and 45 mu M, respectively.

  DOI：

  10.1021/jo00098a048
• 作为产物：
  描述：

  (E)-5-iodo-4-methylpent-4-en-1-ol 在 4-二甲氨基吡啶 、 正丁基锂 、 三乙胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 6.58h， 生成 6-Thia-4,8,13,17,21-pentamethyl-4(E),8(E),12(E),16(E),20-docosapentaenyl tert-butyldimethylsilyl ether
  参考文献：
  名称：

  Synthesis of (6E)-8-Thia- and (14E)-13-Thia-2,3-oxidosqualene: Inhibitors of 2,3-Oxidosqualene-Lanosterol Cyclase

  摘要：

  Synthesis of (6E)-8-thia-2,3-oxidosqualene (22) and (14E)-13-thia-2,3-oxidosqualene (34) as inhibitors of 2,3-oxidosqualene-lanosterol cyclase are reported. Synthesis of 22 required the stereospecific generation of a vinyl sulfide. This was achieved by a new coupling of a benzenethiosulfonate (15) and a lithiated vinyl iodide (18). Synthesis of 34 involved similar coupling of benzenethiosulfonate 29 with lithium reagent obtained from vinyl iodide 33. The required (E)-vinyl iodides 18 and 33 were prepared by zirconium-catalyzed carboalumination of 4-pentyn-1-ol, (16) and 2,6-dimethyl-2(E),6(E)-dien-10-yne (32) respectively. Both 22 and 34 inhibited 2,3-oxidosqualene-lanosterol cyclase from Candida albicans with IC50 values of 0.68 and 45 mu M, respectively.

  DOI：

  10.1021/jo00098a048

文献信息

• Synthesis of (6E)-8-Thia- and (14E)-13-Thia-2,3-oxidosqualene: Inhibitors of 2,3-Oxidosqualene-Lanosterol Cyclase
  作者：Yi Feng Zheng、Allan C. Oehlschlager、Peter G. Hartman

  DOI：10.1021/jo00098a048

  日期：1994.9

  Synthesis of (6E)-8-thia-2,3-oxidosqualene (22) and (14E)-13-thia-2,3-oxidosqualene (34) as inhibitors of 2,3-oxidosqualene-lanosterol cyclase are reported. Synthesis of 22 required the stereospecific generation of a vinyl sulfide. This was achieved by a new coupling of a benzenethiosulfonate (15) and a lithiated vinyl iodide (18). Synthesis of 34 involved similar coupling of benzenethiosulfonate 29 with lithium reagent obtained from vinyl iodide 33. The required (E)-vinyl iodides 18 and 33 were prepared by zirconium-catalyzed carboalumination of 4-pentyn-1-ol, (16) and 2,6-dimethyl-2(E),6(E)-dien-10-yne (32) respectively. Both 22 and 34 inhibited 2,3-oxidosqualene-lanosterol cyclase from Candida albicans with IC50 values of 0.68 and 45 mu M, respectively.