(2S,3S,4R)-2-(4-Methoxy-benzyloxymethoxymethyl)-4-methyl-1-triisopropylsilanyloxy-hex-5-en-3-ol | 152669-30-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (2S,3S,4R)-2-(4-Methoxy-benzyloxymethoxymethyl)-4-methyl-1-triisopropylsilanyloxy-hex-5-en-3-ol
• CAS: 152669-30-2
• 化学式: C₂₆H₄₆O₅Si
• 分子量: 466.734
• InChiKey: MVUUVERDBCSKIM-CWDLOFLHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.18
• 重原子数：
  32.0
• 可旋转键数：
  16.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  57.15
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (2S,3S,4R)-2-(4-Methoxy-benzyloxymethoxymethyl)-4-methyl-1-triisopropylsilanyloxy-hex-5-en-3-ol 在 jones reagent 、 二异丁基氢化铝 、 magnesium bromide 作用下， 以 乙醚 为溶剂， 生成 (2S,3R,4R)-2-(4-Methoxy-benzyloxymethoxymethyl)-4-methyl-1-triisopropylsilanyloxy-hex-5-en-3-ol
  参考文献：
  名称：

  Asymmetric synthesis of all 8 stereoisomers of α-methyl homoallylic alcohols derived by crotyl addition onto bis(hydroxymethyl)acetaldehydes (BHYMA*)

  摘要：

  The asymmetric synthesis of epimeric alpha-methyl homoallylic alcohols 4 and 7 has been realized respectively through chelation-controlled addition of crotyltributyltin to asymmetrized bis(hydroxymethyl)acetaldehydes (BHYMA*) 3, and via chelation-controlled reduction of ketones 8. Due to the stereochemical flexibility of the C-5 chiral centre and to the enantiodivergent preparation of both enantiomers of 3, all 8 isomers of these crotylation products become accessible, starting from an unique precursor 1.

  DOI：

  10.1016/s0040-4039(00)73941-4
• 作为产物：
  描述：

  (S)-3-(4-methoxybenzyloxymethoxy)-2-(triisopropylsilyloxymethyl)-1-propanol 在 草酰氯 、 二甲基亚砜 、 N,N-二异丙基乙胺 、 magnesium bromide 作用下， 以 二氯甲烷 为溶剂， 生成 (2S,3S,4R)-2-(4-Methoxy-benzyloxymethoxymethyl)-4-methyl-1-triisopropylsilanyloxy-hex-5-en-3-ol
  参考文献：
  名称：

  Asymmetric synthesis of all 8 stereoisomers of α-methyl homoallylic alcohols derived by crotyl addition onto bis(hydroxymethyl)acetaldehydes (BHYMA*)

  摘要：

  The asymmetric synthesis of epimeric alpha-methyl homoallylic alcohols 4 and 7 has been realized respectively through chelation-controlled addition of crotyltributyltin to asymmetrized bis(hydroxymethyl)acetaldehydes (BHYMA*) 3, and via chelation-controlled reduction of ketones 8. Due to the stereochemical flexibility of the C-5 chiral centre and to the enantiodivergent preparation of both enantiomers of 3, all 8 isomers of these crotylation products become accessible, starting from an unique precursor 1.

  DOI：

  10.1016/s0040-4039(00)73941-4