(S)-3-((R,E)-2-(tert-butyldimethylsilyloxy)-9-((2R,5S)-5-((5S,8S)-8-((2S,5R)-5-((S)-1-(tert-butyldimethylsilyloxy)undecyl)tetrahydrofuran-2-yl)-2,2,3,3,10,10,11,11-octamethyl-4,9-dioxa-3,10-disiladodecan-5-yl)tetrahydrofuran-2-yl)non-4-enyl)-5-methylfuran-2(5H)-one | 1186497-68-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (S)-3-((R,E)-2-(tert-butyldimethylsilyloxy)-9-((2R,5S)-5-((5S,8S)-8-((2S,5R)-5-((S)-1-(tert-butyldimethylsilyloxy)undecyl)tetrahydrofuran-2-yl)-2,2,3,3,10,10,11,11-octamethyl-4,9-dioxa-3,10-disiladodecan-5-yl)tetrahydrofuran-2-yl)non-4-enyl)-5-methylfuran-2(5H)-one
• 英文别名: (2S)-4-[(E,2R)-9-[(2R,5S)-5-[(1S,4S)-1,4-bis[[tert-butyl(dimethyl)silyl]oxy]-4-[(2S,5R)-5-[(1S)-1-[tert-butyl(dimethyl)silyl]oxyundecyl]oxolan-2-yl]butyl]oxolan-2-yl]-2-[tert-butyl(dimethyl)silyl]oxynon-4-enyl]-2-methyl-2H-furan-5-one
• CAS: 1186497-68-6
• 化学式: C₆₁H₁₂₀O₈Si₄
• 分子量: 1093.96
• InChiKey: SLWBXTCXAKSPAJ-QJDAVABYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  18.72
• 重原子数：
  73
• 可旋转键数：
  36
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  81.7
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (S)-3-((R,E)-2-(tert-butyldimethylsilyloxy)-9-((2R,5S)-5-((5S,8S)-8-((2S,5R)-5-((S)-1-(tert-butyldimethylsilyloxy)undecyl)tetrahydrofuran-2-yl)-2,2,3,3,10,10,11,11-octamethyl-4,9-dioxa-3,10-disiladodecan-5-yl)tetrahydrofuran-2-yl)non-4-enyl)-5-methylfuran-2(5H)-one 在 sodium acetate 、 对甲苯磺酰肼 作用下， 以 乙二醇二甲醚 、 水 为溶剂， 反应 4.0h， 以88%的产率得到(S)-3-((R)-2-(tert-butyldimethylsilyloxy)-9-((2R,5S)-5-((5S,8S)-8-((2S,5R)-5-((S)-1-(tert-butyldimethylsilyloxy)undecyl)tetrahydrofuran-2-yl)-2,2,3,3,10,10,11,11-octamethyl-4,9-dioxa-3,10-disiladodecan-5-yl)tetrahydrofuran-2-yl)nonyl)-5-methylfuran-2(5H)-one
  参考文献：
  名称：

  Concise Syntheses of the Natural Products (+)-Sylvaticin and (+)-cis-Sylvaticin

  摘要：

  Two concise syntheses of the natural products cis-sylvaticin and sylvaticin are reported, using oxidative cyclization methodology as the key step. A sequential solvolysis/hydride shift/intramolecular reduction cascade was used to establish the trans stereochemistry of one of the THF rings of sylvaticin.

  DOI：

  10.1021/ja9049959
• 作为产物：
  描述：

  (S)-3-((R)-2-(tert-butyldimetylsilyloxy)pent-4-enyl)-5-methylfuran-2(5H)-one 、 (5S,8S)-5-((2S,5R)-5-((S)-1-(tert-butyldimethylsilyloxy)undecyl)tetrahydrofuran-2-yl)-8-((2S,5R)-5-(hex-5-enyl)tetrahydrofuran-2-yl)-2,2,3,3,10,10,11,11-octamethyl-4,9-dioxa-3,10-disiladodecane 在 Hoveyda-Grubbs catalyst second generation 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 生成 (S)-3-((R,E)-2-(tert-butyldimethylsilyloxy)-9-((2R,5S)-5-((5S,8S)-8-((2S,5R)-5-((S)-1-(tert-butyldimethylsilyloxy)undecyl)tetrahydrofuran-2-yl)-2,2,3,3,10,10,11,11-octamethyl-4,9-dioxa-3,10-disiladodecan-5-yl)tetrahydrofuran-2-yl)non-4-enyl)-5-methylfuran-2(5H)-one
  参考文献：
  名称：

  Concise Syntheses of the Natural Products (+)-Sylvaticin and (+)-cis-Sylvaticin

  摘要：

  Two concise syntheses of the natural products cis-sylvaticin and sylvaticin are reported, using oxidative cyclization methodology as the key step. A sequential solvolysis/hydride shift/intramolecular reduction cascade was used to establish the trans stereochemistry of one of the THF rings of sylvaticin.

  DOI：

  10.1021/ja9049959