(2S,3R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-3-(2-methoxy-ethoxymethoxy)-hex-5-en-1-ol | 172532-54-6

• 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: (2S,3R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-3-(2-methoxy-ethoxymethoxy)-hex-5-en-1-ol
• 英文别名: (2S,3R)-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-3-(2-methoxyethoxymethoxy)hex-5-en-1-ol
• CAS: 172532-54-6
• 化学式: C₂₇H₄₀O₅Si
• 分子量: 472.697
• InChiKey: ZPFJDAYAIKLTGJ-JYFHCDHNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.75
• 重原子数：
  33
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 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)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-3-(2-methoxy-ethoxymethoxy)-hex-5-en-1-ol 在 草酰氯 、 二甲基亚砜 、 N,N-二异丙基乙胺 作用下， 生成 (2S,3R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-3-(2-methoxy-ethoxymethoxy)-hex-5-enal
  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-Butyldiphenylsilyl)oxy>-2-<<<(p-methoxybenzyl)oxy>methoxy>methyl>-5-hexen-3-on 在 4 A molecular sieve 、 pH 7 buffer (KH₂PO₄-K₂HPO₄) 、 四丁基碘化铵 、 二异丁基氢化铝 、 N,N-二异丙基乙胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 magnesium bromide 、 叔丁醇 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.5h， 生成 (2S,3R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-3-(2-methoxy-ethoxymethoxy)-hex-5-en-1-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.