(3S,4S)-Methyl 5-Cyclohexyl-3-(dimethylphenylsilyl)-4-phthalimidopentanoate | 131973-33-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: (3S,4S)-Methyl 5-Cyclohexyl-3-(dimethylphenylsilyl)-4-phthalimidopentanoate
• 英文别名: methyl (3S,4S)-5-cyclohexyl-3-[dimethyl(phenyl)silyl]-4-(1,3-dioxoisoindol-2-yl)pentanoate
• CAS: 131973-33-6
• 化学式: C₂₈H₃₅NO₄Si
• 分子量: 477.676
• InChiKey: LZIWOIHEVMRECL-DQEYMECFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.17
• 重原子数：
  34.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  63.68
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (3S,4S)-Methyl 5-Cyclohexyl-3-(dimethylphenylsilyl)-4-phthalimidopentanoate 在 四氟硼酸-二乙醚络合物 、 potassium fluoride 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 (3S,4S)-Methyl 5-Cyclohexyl-3-hydroxy-4-phthalimidopentanoate
  参考文献：
  名称：

  Optically active building blocks from the SPAC reaction: a completely asymmetric synthesis of (4S-cis)-5-(cyclohexylmethyl)-4-hydroxy-2-pyrrolidinone, a statine analog

  摘要：

  Factors that govern chemical and optical yields of methyl gamma-hydroxy-alpha,beta-unsaturated esters 1 formed in reactions of optically active sulfinylacetates 2 with aldehydes (the ''SPAC'' reaction) are defined. Racemic samples of these chirons (1) can be resolved via acylations mediated by crude preparations of the lipase Pseudomonas K-10 in organic solvents. Combinations of asymmetric SPAC reactions with these biocatalytic resolutions provide routes to highly optically active esters 1 in good yields. This methodology is applied in a completely asymmetric synthesis of (4S-cis)-5-(cyclohexylmethyl)-4-hydroxy-2-pyrrolidinone (15), a cyclic derivative of (3S,4S)-4-amino-5-cyclohexyl-3-hydroxypentanoic acid (ACHPA).

  DOI：

  10.1021/jo00006a017
• 作为产物：
  描述：

  环己基乙醛 在 哌啶 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 34.0h， 生成 (3S,4S)-Methyl 5-Cyclohexyl-3-(dimethylphenylsilyl)-4-phthalimidopentanoate
  参考文献：
  名称：

  Optically active building blocks from the SPAC reaction: a completely asymmetric synthesis of (4S-cis)-5-(cyclohexylmethyl)-4-hydroxy-2-pyrrolidinone, a statine analog

  摘要：

  Factors that govern chemical and optical yields of methyl gamma-hydroxy-alpha,beta-unsaturated esters 1 formed in reactions of optically active sulfinylacetates 2 with aldehydes (the ''SPAC'' reaction) are defined. Racemic samples of these chirons (1) can be resolved via acylations mediated by crude preparations of the lipase Pseudomonas K-10 in organic solvents. Combinations of asymmetric SPAC reactions with these biocatalytic resolutions provide routes to highly optically active esters 1 in good yields. This methodology is applied in a completely asymmetric synthesis of (4S-cis)-5-(cyclohexylmethyl)-4-hydroxy-2-pyrrolidinone (15), a cyclic derivative of (3S,4S)-4-amino-5-cyclohexyl-3-hydroxypentanoic acid (ACHPA).

  DOI：

  10.1021/jo00006a017

文献信息

• BURGESS, KEVIN;CASSIDY, JUANITA;HENDERSON, IAN, J. ORG. CHEM., 56,(1991) N, C. 2050-2058
  作者：BURGESS, KEVIN、CASSIDY, JUANITA、HENDERSON, IAN

  DOI：——

  日期：——