(3S,4R)-tert-Butyl 3--5-((tert-butyldimethylsilyl)oxy)-4-methylpentanoate | 162398-20-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3S,4R)-tert-Butyl 3--5-((tert-butyldimethylsilyl)oxy)-4-methylpentanoate
• 英文别名: tert-butyl (3S,4R)-3-[benzyl-[(1R)-1-phenylethyl]amino]-5-[tert-butyl(dimethyl)silyl]oxy-4-methylpentanoate
• CAS: 162398-20-1
• 化学式: C₃₁H₄₉NO₃Si
• 分子量: 511.82
• InChiKey: CEIJAUSNSDEUDW-OARDWFSCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.01
• 重原子数：
  36
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3S,4R)-tert-Butyl 3--5-((tert-butyldimethylsilyl)oxy)-4-methylpentanoate 在 palladium dihydroxide 氢气 作用下， 以73%的产率得到(3S,4R)-tert-Butyl 3-Amino-5-(tert-butyldimethylsiloxy)-4-methylpentanoate
  参考文献：
  名称：

  A Three Component Coupling Approach to a Chiral 1.beta.-Methylcarbapenem Key Intermediate

  摘要：

  Conjugate addition of N-benzyl-N((R)-1-phenylethyl)amine (R)-5 to (R)-(E)-tert-butyl 5-((tert-butyldimethylsilyl)oxy)-4-methyl-2-pentenoate (10a) produced the (3S,4R)-syn-adduct 14 with essentially 100% de in 84% yield, whereas the addition of (S)-5 to 10a afforded the (3R,4R)-anti-adduct 15 with essentially 100% de in 95% yield. The syn adduct 14 was converted upon sequential treatment with lithium diisopropylamide-methylaluminum dichloride-acetaldehyde to the key intermediate 21; the diastereoisomer ratio of 21 to other diasteroisomers was 80:20. Conversion of 21 to a 1 beta-methylcarbapenem key intermediate 26 was carried out readily according to the known procedures.

  DOI：

  10.1021/jo00106a027
• 作为产物：
  描述：

  (S)-3-(tert-butyldimethylsilyloxy)-2-methylpropionic acid methyl ester 在 正丁基锂 、 二异丁基氢化铝 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 7.0h， 生成 (3S,4R)-tert-Butyl 3--5-((tert-butyldimethylsilyl)oxy)-4-methylpentanoate
  参考文献：
  名称：

  A Three Component Coupling Approach to a Chiral 1.beta.-Methylcarbapenem Key Intermediate

  摘要：

  Conjugate addition of N-benzyl-N((R)-1-phenylethyl)amine (R)-5 to (R)-(E)-tert-butyl 5-((tert-butyldimethylsilyl)oxy)-4-methyl-2-pentenoate (10a) produced the (3S,4R)-syn-adduct 14 with essentially 100% de in 84% yield, whereas the addition of (S)-5 to 10a afforded the (3R,4R)-anti-adduct 15 with essentially 100% de in 95% yield. The syn adduct 14 was converted upon sequential treatment with lithium diisopropylamide-methylaluminum dichloride-acetaldehyde to the key intermediate 21; the diastereoisomer ratio of 21 to other diasteroisomers was 80:20. Conversion of 21 to a 1 beta-methylcarbapenem key intermediate 26 was carried out readily according to the known procedures.

  DOI：

  10.1021/jo00106a027

文献信息

• A Three Component Coupling Approach to a Chiral 1.beta.-Methylcarbapenem Key Intermediate
  作者：Naofumi Tsukada、Takashi Shimada、Young Soo Gyoung、Naoki Asao、Yoshinori Yamamoto

  DOI：10.1021/jo00106a027

  日期：1995.1

  Conjugate addition of N-benzyl-N((R)-1-phenylethyl)amine (R)-5 to (R)-(E)-tert-butyl 5-((tert-butyldimethylsilyl)oxy)-4-methyl-2-pentenoate (10a) produced the (3S,4R)-syn-adduct 14 with essentially 100% de in 84% yield, whereas the addition of (S)-5 to 10a afforded the (3R,4R)-anti-adduct 15 with essentially 100% de in 95% yield. The syn adduct 14 was converted upon sequential treatment with lithium diisopropylamide-methylaluminum dichloride-acetaldehyde to the key intermediate 21; the diastereoisomer ratio of 21 to other diasteroisomers was 80:20. Conversion of 21 to a 1 beta-methylcarbapenem key intermediate 26 was carried out readily according to the known procedures.