(E)-3-[(1R,2S,3S,3aR,4S,5R,7aS)-1-(tert-Butyl-dimethyl-silanyloxy)-5-[3-(tert-butyl-dimethyl-silanyloxy)-butyl]-3-(tert-butyl-diphenyl-silanyloxy)-2-methyl-2,3,3a,4,5,7a-hexahydro-1H-inden-4-yl]-acrylic acid methyl ester | 794568-14-2

• 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: (E)-3-[(1R,2S,3S,3aR,4S,5R,7aS)-1-(tert-Butyl-dimethyl-silanyloxy)-5-[3-(tert-butyl-dimethyl-silanyloxy)-butyl]-3-(tert-butyl-diphenyl-silanyloxy)-2-methyl-2,3,3a,4,5,7a-hexahydro-1H-inden-4-yl]-acrylic acid methyl ester
• CAS: 794568-14-2
• 化学式: C₄₆H₇₄O₅Si₃
• 分子量: 791.347
• InChiKey: VAGQHYYUKGYGIW-PYXJHDJOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.93
• 重原子数：
  54.0
• 可旋转键数：
  13.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  53.99
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (E)-3-[(1R,2S,3S,3aR,4S,5R,7aS)-1-(tert-Butyl-dimethyl-silanyloxy)-5-[3-(tert-butyl-dimethyl-silanyloxy)-butyl]-3-(tert-butyl-diphenyl-silanyloxy)-2-methyl-2,3,3a,4,5,7a-hexahydro-1H-inden-4-yl]-acrylic acid methyl ester 在 N-甲基吲哚酮 、 四丙基高钌酸铵 、 camphor-10-sulfonic acid 、 四丁基氟化铵 、 六甲基二硅氮烷 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 17.67h， 生成 [(1S,2R,3aR,5aS,6R,7S,8S,8aR,8bR)-2-Acetyl-6-(tert-butyl-dimethyl-silanyloxy)-8-(tert-butyl-diphenyl-silanyloxy)-7-methyl-1,2,3,3a,5a,6,7,8,8a,8b-decahydro-as-indacen-1-yl]-acetic acid methyl ester
  参考文献：
  名称：

  Synthesis of the A,B,C-Ring System of Hexacyclinic Acid

  摘要：

  [GRAPHICS]The synthesis of the A,B,C-ring system (2) of hexacyclinic acid (1) is achieved starting from a selective Diels-Alder reaction followed by vinyl cuprate addition. The diastereoselective reduction of the ketone carbonyl at C16 could be achieved with LiAlH4. An intramolecular Michael addition established the ring system stereoselectively, providing access to the selective generation of 9 out of the 14 stereocenters of hexacyclinic acid.

  DOI：

  10.1021/ol048720o
• 作为产物：
  描述：

  (2S,3R,3aS,6R)-3-[tert-butyl(dimethyl)silyl]oxy-6-[3-[tert-butyl(dimethyl)silyl]oxybutyl]-2-methyl-2,3,3a,6-tetrahydroinden-1-one 在 Hoveyda-Grubbs catalyst second generation 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 copper(I) bromide dimethylsulfide complex 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 214.5h， 生成 (E)-3-[(1R,2S,3S,3aR,4S,5R,7aS)-1-(tert-Butyl-dimethyl-silanyloxy)-5-[3-(tert-butyl-dimethyl-silanyloxy)-butyl]-3-(tert-butyl-diphenyl-silanyloxy)-2-methyl-2,3,3a,4,5,7a-hexahydro-1H-inden-4-yl]-acrylic acid methyl ester
  参考文献：
  名称：

  Synthesis of the A,B,C-Ring System of Hexacyclinic Acid

  摘要：

  [GRAPHICS]The synthesis of the A,B,C-ring system (2) of hexacyclinic acid (1) is achieved starting from a selective Diels-Alder reaction followed by vinyl cuprate addition. The diastereoselective reduction of the ketone carbonyl at C16 could be achieved with LiAlH4. An intramolecular Michael addition established the ring system stereoselectively, providing access to the selective generation of 9 out of the 14 stereocenters of hexacyclinic acid.

  DOI：

  10.1021/ol048720o