<3(S,R),4(S,R)>-2-<<(tert-butyldimethylsilyl)oxy>imino>-4-hydroxy-4-(4-methoxyphenyl)-3-methyl-N-tert-butylbutanamide | 131565-18-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: <3(S,R),4(S,R)>-2-<<(tert-butyldimethylsilyl)oxy>imino>-4-hydroxy-4-(4-methoxyphenyl)-3-methyl-N-tert-butylbutanamide
• 英文别名: (3(S,R),4(S,R))-2-{[(tert-butyldimethylsilyl)oxy]imino}-4-hydroxy-4-(4-methoxyphenyl)-3-methyl-N-tert-butylbutanamide
• CAS: 131565-18-9
• 化学式: C₂₂H₃₈N₂O₄Si
• 分子量: 422.64
• InChiKey: XNZRIFYQLSWANR-KXBFYZLASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.66
• 重原子数：
  29.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  80.15
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  <3(S,R),4(S,R)>-2-<<(tert-butyldimethylsilyl)oxy>imino>-4-hydroxy-4-(4-methoxyphenyl)-3-methyl-N-tert-butylbutanamide 、 苯甲酰氯 在 红铝 作用下， 生成 <2(S,R),3(S,R),4(S,R)>-2-benzamido-4-hydroxy-4-(4-methoxyphenyl)-3-methyl-N-tert-butylbutanamide
  参考文献：
  名称：

  .alpha.-Oximino amide trianions in the stereoselective synthesis of isoxazolines and .gamma.-hydroxy .alpha.-amino acids

  摘要：

  The trianions 17 and 33, which were prepared from the corresponding alpha-oximino amides 7 and 30, were reacted with 4-methoxybenzaldehyde to stereoselectively provide, on acidification, the corresponding trans-substituted isoxazoline-3-carboxamides 8 and 31/32, respectively. Additionally, the dianion 24, which was prepared from the corresponding O-silyl oxime 22, was reacted with 4-methoxybenzaldehyde to stereoselectively give the anti beta-hydroxy oxime 23. Reduction of 8 and 26 stereoselectively gave the 2,3-syn-3,4-anti amino amides 11 and 27. Amides 11 and 27 were subsequently converted to the gamma-hydroxy-alpha-amino acids 12 and 29 and the corresponding lactones 13 and 28. Amino acid 29 is the N-terminal amino acid of the antifungal agent nikkomycin B.

  DOI：

  10.1021/jo00005a042
• 作为产物：
  描述：

  N-tert-butyl-2-(hydroxyimino)butanamide 在 咪唑 、 四甲基乙二胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 正戊烷 为溶剂， 反应 19.5h， 生成 <3(S,R),4(S,R)>-2-<<(tert-butyldimethylsilyl)oxy>imino>-4-hydroxy-4-(4-methoxyphenyl)-3-methyl-N-tert-butylbutanamide
  参考文献：
  名称：

  .alpha.-Oximino amide trianions in the stereoselective synthesis of isoxazolines and .gamma.-hydroxy .alpha.-amino acids

  摘要：

  The trianions 17 and 33, which were prepared from the corresponding alpha-oximino amides 7 and 30, were reacted with 4-methoxybenzaldehyde to stereoselectively provide, on acidification, the corresponding trans-substituted isoxazoline-3-carboxamides 8 and 31/32, respectively. Additionally, the dianion 24, which was prepared from the corresponding O-silyl oxime 22, was reacted with 4-methoxybenzaldehyde to stereoselectively give the anti beta-hydroxy oxime 23. Reduction of 8 and 26 stereoselectively gave the 2,3-syn-3,4-anti amino amides 11 and 27. Amides 11 and 27 were subsequently converted to the gamma-hydroxy-alpha-amino acids 12 and 29 and the corresponding lactones 13 and 28. Amino acid 29 is the N-terminal amino acid of the antifungal agent nikkomycin B.

  DOI：

  10.1021/jo00005a042

文献信息

• Novel anionic reagents for the stereoselective synthesis of γ-hydroxy-α-amino-acids. An X-ray crystallographic study of 2R(S)-benzoylamino-N-t-butyl-4R(S)-hydroxy-4-(4-methoxyphenyl)-3R(S)-methylbutanamide
  作者：Bernard J. Banks、Anthony G. M. Barrett、Mark A. Russell、David J. Williams

  DOI：10.1039/c39830000873

  日期：——

  e2-But)CONHBut, prepared respectively from 4-methoxybenzaldehyde (ArCHO) and the anions MeCHC-(–)C(NBut) and MeCHC(–OSiMe2But)C(NBut), were reduced stereoselectively (25:1) and benzoylated to produce the title amide which was characterized by an X-ray analysis.

  异恶唑啉的反式-Ar [图形省略]）CONHBu吨和肟苏-ARCH（OH）CH（Me）的C（NOSiMe 2 -Bu吨）CONHBu吨，由4-甲氧基苯甲醛（ArCHO）和阴离子分别机甲制备C-将（– ）C（NBu t）和MeCH C（–OSiMe 2 Bu t）C（NBu t）进行立体选择性还原（25：1）和苯甲酰化，生成标题酰胺，通过X射线分析对其进行表征。