tert-butyl-dimethyl-[(3S,4R,5R)-3,5,7-trimethyloct-1-en-4-yl]oxysilane | 618448-99-0

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: tert-butyl-dimethyl-[(3S,4R,5R)-3,5,7-trimethyloct-1-en-4-yl]oxysilane
• CAS: 618448-99-0
• 化学式: C₁₇H₃₆OSi
• 分子量: 284.558
• InChiKey: URVBWDOCAZDZDW-XHSDSOJGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.88
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  tert-butyl-dimethyl-[(3S,4R,5R)-3,5,7-trimethyloct-1-en-4-yl]oxysilane 在 ruthenium trichloride 、 sodium periodate 作用下， 以 四氯化碳 、 乙腈 为溶剂， 以98%的产率得到(2R,3R,4R)-3-(tert-butyldimethylsilyloxy)-2,4,6-trimethylheptanoic acid
  参考文献：
  名称：

  Asymmetric Synthesis of Four Diastereomers of 3-Hydroxy-2,4,6-trimethylheptanoic Acid:  Proof of Configurational Assignment

  摘要：

  Four unique diastereomers of 3-hydroxy-2,4,6-trimethylheptanoic acid-(2R,3R,4R), (2S,3R,4R), (2S,3R,4S), and (2R,3R,4S)-the fatty acid component of callipeltin A and D, have been synthesized from commercially available (+)- and (-)-pseudoephedrine propionamide in 6 steps and 59% average overall yield. Comparison of the H-1 and C-13 NMR and optical rotation data of the resulting isomers with the natural fragment unambiguously verifies the configurational assignment of the natural isomer as (2R,3R,4R).

  DOI：

  10.1021/jo034738l
• 作为产物：
  描述：

  (R)-N-((1S,2S)-1-hydroxy-1-phenylpropan-2-yl)-N,2,4-trimethylpentanamide 在 咪唑 、 lithium aluminium tetrahydride 、 三氟化硼乙醚 、 乙酸乙酯 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 tert-butyl-dimethyl-[(3S,4R,5R)-3,5,7-trimethyloct-1-en-4-yl]oxysilane
  参考文献：
  名称：

  Asymmetric Synthesis of Four Diastereomers of 3-Hydroxy-2,4,6-trimethylheptanoic Acid:  Proof of Configurational Assignment

  摘要：

  Four unique diastereomers of 3-hydroxy-2,4,6-trimethylheptanoic acid-(2R,3R,4R), (2S,3R,4R), (2S,3R,4S), and (2R,3R,4S)-the fatty acid component of callipeltin A and D, have been synthesized from commercially available (+)- and (-)-pseudoephedrine propionamide in 6 steps and 59% average overall yield. Comparison of the H-1 and C-13 NMR and optical rotation data of the resulting isomers with the natural fragment unambiguously verifies the configurational assignment of the natural isomer as (2R,3R,4R).

  DOI：

  10.1021/jo034738l