(2S,3R)-1-(tert-Butyl-dimethyl-silanyloxy)-2-(4-methoxy-benzyloxymethoxymethyl)-hex-5-en-3-ol | 172532-53-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (2S,3R)-1-(tert-Butyl-dimethyl-silanyloxy)-2-(4-methoxy-benzyloxymethoxymethyl)-hex-5-en-3-ol
• 英文别名: (2S,3R)-1-[tert-butyl(dimethyl)silyl]oxy-2-[(4-methoxyphenyl)methoxymethoxymethyl]hex-5-en-3-ol
• CAS: 172532-53-5
• 化学式: C₂₂H₃₈O₅Si
• 分子量: 410.626
• InChiKey: ITBRSQBBADRPKH-PZJWPPBQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.76
• 重原子数：
  28
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,3R)-1-(tert-Butyl-dimethyl-silanyloxy)-2-(4-methoxy-benzyloxymethoxymethyl)-hex-5-en-3-ol 在 2,6-二甲基吡啶 、 草酰氯 、 4 A molecular sieve 、 对甲苯磺酸 、 二甲基亚砜 、 N,N-二异丙基乙胺 、 magnesium bromide 作用下， 以 二氯甲烷 、 异丙醇 为溶剂， 反应 36.08h， 生成 (4S,5S,6R)-5-(4-Methoxy-benzyloxymethoxymethyl)-6-triisopropylsilanyloxy-nona-1,8-dien-4-ol
  参考文献：
  名称：

  Highly Versatile Stereoselective Synthesis of All Eight Stereoisomers of Branched-Chain Triols Starting from Asymmetrized Bis(hydroxymethyl)acetaldehydes (BHYMA)

  摘要：

  All possible stereoisomers of triols of general formula 5 (R(1) allyl, R(2) = Me or allyl) have been synthesized stereoselectively starting from asymmetrized bis(hydroxymethyl)acetaldehyde (BHY-MA*), a novel chiral building block prepared through a chemoenzymatic methodology. This goal was realized through a sequence of protecting group-controlled nucleophilic additions and/or reductions performed on two side arms of this versatile building block.

  DOI：

  10.1021/jo00129a029
• 作为产物：
  描述：

  (S)-1-(tert-Butyl-dimethyl-silanyloxy)-2-(4-methoxy-benzyloxymethoxymethyl)-hex-5-en-3-ol 在 草酰氯 、 4 A molecular sieve 、 二异丁基氢化铝 、 二甲基亚砜 、 三乙胺 、 magnesium bromide 作用下， 反应 3.67h， 生成 (2S,3R)-1-(tert-Butyl-dimethyl-silanyloxy)-2-(4-methoxy-benzyloxymethoxymethyl)-hex-5-en-3-ol
  参考文献：
  名称：

  Highly Versatile Stereoselective Synthesis of All Eight Stereoisomers of Branched-Chain Triols Starting from Asymmetrized Bis(hydroxymethyl)acetaldehydes (BHYMA)

  摘要：

  All possible stereoisomers of triols of general formula 5 (R(1) allyl, R(2) = Me or allyl) have been synthesized stereoselectively starting from asymmetrized bis(hydroxymethyl)acetaldehyde (BHY-MA*), a novel chiral building block prepared through a chemoenzymatic methodology. This goal was realized through a sequence of protecting group-controlled nucleophilic additions and/or reductions performed on two side arms of this versatile building block.

  DOI：

  10.1021/jo00129a029

文献信息

• Highly Versatile Stereoselective Synthesis of All Eight Stereoisomers of Branched-Chain Triols Starting from Asymmetrized Bis(hydroxymethyl)acetaldehydes (BHYMA)
  作者：Luca Banfi、Giuseppe Guanti、Maria Teresa Zannetti

  DOI：10.1021/jo00129a029

  日期：1995.12

  All possible stereoisomers of triols of general formula 5 (R(1) allyl, R(2) = Me or allyl) have been synthesized stereoselectively starting from asymmetrized bis(hydroxymethyl)acetaldehyde (BHY-MA*), a novel chiral building block prepared through a chemoenzymatic methodology. This goal was realized through a sequence of protecting group-controlled nucleophilic additions and/or reductions performed on two side arms of this versatile building block.