(S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-(4-methoxy-benzyloxymethoxymethyl)-propionaldehyde | 152669-29-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-(4-methoxy-benzyloxymethoxymethyl)-propionaldehyde
• 英文别名: (2S)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-3-[(4-methoxyphenyl)methoxymethoxy]propanal
• CAS: 152669-29-9
• 化学式: C₁₉H₃₂O₅Si
• 分子量: 368.546
• InChiKey: BQIMVWWINUUZFS-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.02
• 重原子数：
  25.0
• 可旋转键数：
  11.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  53.99
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-(4-methoxy-benzyloxymethoxymethyl)-propionaldehyde 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,4R)-1-(tert-Butyl-dimethyl-silanyloxy)-2-(4-methoxy-benzyloxymethoxymethyl)-4-methyl-hex-5-en-3-one
  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-(tert-Butyl-dimethyl-silanyloxy)-2-(4-methoxy-benzyloxymethoxymethyl)-propan-1-ol 在 草酰氯 、 二甲基亚砜 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 (S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-(4-methoxy-benzyloxymethoxymethyl)-propionaldehyde
  参考文献：
  名称：

  使用DIBALH / MgBr 2系统，由保护基控制的非对映选择性还原衍生自THYM *的双保护α，α-双（羟甲基）酮

  摘要：

  新型手性结构单元THYM * 1和BHYMA * 2衍生的双保护α，α-双（羟甲基）酮5的还原反应具有良好的立体选择性（从85:15至97：3）。通过采用DIBALH和MgBr的组合两个保护基团和适当的选择2 ·的Et 2 O.

  DOI：

  10.1016/s0040-4039(00)73940-2

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.