(R_S,3S)-4-methyl-3-(2-methylpropane-2-sulfinylamino)pentanoic acid | 477586-98-4

• 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: (R_S,3S)-4-methyl-3-(2-methylpropane-2-sulfinylamino)pentanoic acid
• 英文别名: (3S)-3-[[(R)-tert-butylsulfinyl]amino]-4-methylpentanoic acid
• CAS: 477586-98-4
• 化学式: C₁₀H₂₁NO₃S
• 分子量: 235.348
• InChiKey: BLLBMBDAFAZYNE-VXJOIVPMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  85.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (R_S,3R)-3-(2-methylpropane-2-sulfinylamino)butyric acid 、 (R_S,3S)-4-methyl-3-(2-methylpropane-2-sulfinylamino)pentanoic acid 、 (R_S,3R)-5-methyl-3-(2-methylpropane-2-sulfinylamino)hexanoic acid 生成 3-[3-(3-{3-[3-(3-amino-4-methylpentanoylamino)butyrylamino]-5-methylhexanoylamino}-4-methylpentanoylamino)butyrylamino]-5-methylhexanoic acid amide
  参考文献：
  名称：

  Asymmetric Synthesis of β-Amino Acid Derivatives Incorporating a Broad Range of Substitution Patterns by Enolate Additions to tert-Butanesulfinyl Imines

  摘要：

  Addition of Ti(Oi-Pr)(3) ester enolates to tert-butanesulfinyl aldimines and ketimines provided beta-substituted, alpha,beta- and beta,beta-disubstituted, alpha,beta,beta- and alpha,alpha,beta-trisubstituted, and alpha,alpha,beta,beta-tetrasubstituted beta-amino acid derivatives in high yields and with high diastereoselectivites. The N-sulfinyl-beta-amino ester products were further employed as versatile intermediates for both standard solution-phase and solid-phase synthetic transformations, including the synthesis of beta-peptide foldamers.

  DOI：

  10.1021/jo025957u
• 作为产物：
  描述：

  (R,E)-2-methyl-N-(2-methylpropylidene)propane-2-sulfinamide 在 lithium hydroxide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 28.0h， 生成 (R_S,3S)-4-methyl-3-(2-methylpropane-2-sulfinylamino)pentanoic acid
  参考文献：
  名称：

  Asymmetric Synthesis of β-Amino Acid Derivatives Incorporating a Broad Range of Substitution Patterns by Enolate Additions to tert-Butanesulfinyl Imines

  摘要：

  Addition of Ti(Oi-Pr)(3) ester enolates to tert-butanesulfinyl aldimines and ketimines provided beta-substituted, alpha,beta- and beta,beta-disubstituted, alpha,beta,beta- and alpha,alpha,beta-trisubstituted, and alpha,alpha,beta,beta-tetrasubstituted beta-amino acid derivatives in high yields and with high diastereoselectivites. The N-sulfinyl-beta-amino ester products were further employed as versatile intermediates for both standard solution-phase and solid-phase synthetic transformations, including the synthesis of beta-peptide foldamers.

  DOI：

  10.1021/jo025957u

文献信息

• Asymmetric Synthesis of β-Amino Acid Derivatives Incorporating a Broad Range of Substitution Patterns by Enolate Additions to <i>tert</i>-Butanesulfinyl Imines
  作者：Tony P. Tang、Jonathan A. Ellman

  DOI：10.1021/jo025957u

  日期：2002.11.1

  Addition of Ti(Oi-Pr)(3) ester enolates to tert-butanesulfinyl aldimines and ketimines provided beta-substituted, alpha,beta- and beta,beta-disubstituted, alpha,beta,beta- and alpha,alpha,beta-trisubstituted, and alpha,alpha,beta,beta-tetrasubstituted beta-amino acid derivatives in high yields and with high diastereoselectivites. The N-sulfinyl-beta-amino ester products were further employed as versatile intermediates for both standard solution-phase and solid-phase synthetic transformations, including the synthesis of beta-peptide foldamers.