(1S,2S,3R,6R)-2-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-propyl]-6-isopropyl-3-methyl-cyclohexanol | 210291-44-4

• 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: (1S,2S,3R,6R)-2-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-propyl]-6-isopropyl-3-methyl-cyclohexanol
• CAS: 210291-44-4
• 化学式: C₁₉H₄₀O₂Si
• 分子量: 328.611
• InChiKey: NBDUCOCSXKVPPZ-ZKXLYKBJSA-N

物化性质

• 沸点：
  364.932±15.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  0.891±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

反应信息

• 作为反应物：
  描述：

  (1S,2S,3R,6R)-2-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-propyl]-6-isopropyl-3-methyl-cyclohexanol 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以94%的产率得到(1'R,1S,2R,3R,6R)-2-(1'-hydroxypropyl)-6-isopropyl-3-methylcyclohexanol
  参考文献：
  名称：

  Synthesis and proof of stereostructure of a new (+)-isomenthone-derived homochiral 1,3-diol

  摘要：

  Diastereopure (+)-isomenthone-derived ketoalcohol 2 was converted to the homochiral 1,3-diol 6 either by direct reduction or reduction of silyl protected derivatives. The diastereomeric preference of the reduction was the same in all cases. Reduction of 2 with NaBH4 gave essentially a single diastereomer, while reduction with LiAlH4 gave similar to 6:1 selectivity in favour of the same diastereomer. Reduction of the silyl protected substrates 7 and 8 gave, after column chromatography, 98% yield of a single diastereomer, desilylation of which established this to be the same; diastereomer as obtained through hydride reductions of unprotected 2. The structure of diol 6 was proven through coupling data and NOE experiments at 600 MHz. Overall, two stereochemistry introducing steps have elaborated the two stereogenic centres of (+)-isomenthone to the five contiguous stereogenic centres of 6. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00013-5
• 作为产物：
  描述：

  (2R,3R,6R)-2-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-propyl]-6-isopropyl-3-methyl-cyclohexanone 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以98%的产率得到(1S,2S,3R,6R)-2-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-propyl]-6-isopropyl-3-methyl-cyclohexanol
  参考文献：
  名称：

  Synthesis and proof of stereostructure of a new (+)-isomenthone-derived homochiral 1,3-diol

  摘要：

  Diastereopure (+)-isomenthone-derived ketoalcohol 2 was converted to the homochiral 1,3-diol 6 either by direct reduction or reduction of silyl protected derivatives. The diastereomeric preference of the reduction was the same in all cases. Reduction of 2 with NaBH4 gave essentially a single diastereomer, while reduction with LiAlH4 gave similar to 6:1 selectivity in favour of the same diastereomer. Reduction of the silyl protected substrates 7 and 8 gave, after column chromatography, 98% yield of a single diastereomer, desilylation of which established this to be the same; diastereomer as obtained through hydride reductions of unprotected 2. The structure of diol 6 was proven through coupling data and NOE experiments at 600 MHz. Overall, two stereochemistry introducing steps have elaborated the two stereogenic centres of (+)-isomenthone to the five contiguous stereogenic centres of 6. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00013-5