(S)-2-[(3R,4S)-4-(tert-Butyl-diphenyl-silanyloxy)-3-hydroxy-5-phenyl-pentanoylamino]-3-methyl-butyric acid methyl ester | 185100-52-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-2-[(3R,4S)-4-(tert-Butyl-diphenyl-silanyloxy)-3-hydroxy-5-phenyl-pentanoylamino]-3-methyl-butyric acid methyl ester
• 英文别名: methyl (2S)-2-[[(3R,4S)-4-[tert-butyl(diphenyl)silyl]oxy-3-hydroxy-5-phenylpentanoyl]amino]-3-methylbutanoate
• CAS: 185100-52-1
• 化学式: C₃₃H₄₃NO₅Si
• 分子量: 561.794
• InChiKey: LTEMNWBNKWGJFE-HZFRXHCASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.24
• 重原子数：
  40
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-2-[(3R,4S)-4-(tert-Butyl-diphenyl-silanyloxy)-3-hydroxy-5-phenyl-pentanoylamino]-3-methyl-butyric acid methyl ester 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以90%的产率得到methyl (2S)-2-[[(3R,4S)-3,4-dihydroxy-5-phenylpentanoyl]amino]-3-methylbutanoate
  参考文献：
  名称：

  New Approach to the Coupling of γ-Amino β-Hydroxy Acids and β,γ-Dihydroxy Acids with α-Amino Acid Esters

  摘要：

  alpha,alpha-Dichloro beta-lactones, readily obtained by a highly diastereoselective cycloaddition of dichloroketene to N-Boc-alpha-amino aldehydes and alpha-(silyloxy) aldehydes, coupled efficiently with alpha-amino acid esters leading, after dehalogenation with H-2 over 10% Pd on charcoal, to peptide mimics under mild reaction conditions.

  DOI：

  10.1021/jo961219s
• 作为产物：
  描述：

  2(S)-<(tert-butyldiphenylsilyl)oxy>-3-phenylpropanal 在 氢气 、 铜 、 三乙胺 、 锌 作用下， 以 乙醚 为溶剂， 反应 43.0h， 生成 (S)-2-[(3R,4S)-4-(tert-Butyl-diphenyl-silanyloxy)-3-hydroxy-5-phenyl-pentanoylamino]-3-methyl-butyric acid methyl ester
  参考文献：
  名称：

  New Approach to the Coupling of γ-Amino β-Hydroxy Acids and β,γ-Dihydroxy Acids with α-Amino Acid Esters

  摘要：

  alpha,alpha-Dichloro beta-lactones, readily obtained by a highly diastereoselective cycloaddition of dichloroketene to N-Boc-alpha-amino aldehydes and alpha-(silyloxy) aldehydes, coupled efficiently with alpha-amino acid esters leading, after dehalogenation with H-2 over 10% Pd on charcoal, to peptide mimics under mild reaction conditions.

  DOI：

  10.1021/jo961219s

文献信息

• New Approach to the Coupling of γ-Amino β-Hydroxy Acids and β,γ-Dihydroxy Acids with α-Amino Acid Esters
  作者：Claudio Palomo、José I. Miranda、Anthony Linden

  DOI：10.1021/jo961219s

  日期：1996.1.1

  alpha,alpha-Dichloro beta-lactones, readily obtained by a highly diastereoselective cycloaddition of dichloroketene to N-Boc-alpha-amino aldehydes and alpha-(silyloxy) aldehydes, coupled efficiently with alpha-amino acid esters leading, after dehalogenation with H-2 over 10% Pd on charcoal, to peptide mimics under mild reaction conditions.