(R_S,2S,3S)-(-)-2-methyl-3-(2-methylpropane-2-sulfinylamino)-3-phenylpropionic acid methyl ester

• 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,2S,3S)-(-)-2-methyl-3-(2-methylpropane-2-sulfinylamino)-3-phenylpropionic acid methyl ester
• 英文别名: (2S,3S)-methyl 3-((R)-1,1-dimethylethylsulfinamido)-2-methyl-3-phenylpropanoate；methyl (2S,3S)-3-[[(R)-tert-butylsulfinyl]amino]-2-methyl-3-phenylpropanoate
• 化学式: C₁₅H₂₃NO₃S
• 分子量: 297.419
• InChiKey: YVVKVNKUBRRPEG-HGFQGUBDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  74.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  丙酸甲酯 、 (R,E)-2-methyl-N-(phenylmethylene)-2-propanesulfinamide 在 lithium diisopropyl amide 、 三异丙氧基氯化钛 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以85%的产率得到(R_S,2S,3S)-(-)-2-methyl-3-(2-methylpropane-2-sulfinylamino)-3-phenylpropionic acid methyl ester
  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

• Endomorphin-1 analogs containing α-methyl-β-amino acids exhibit potent analgesic activity after peripheral administration
  作者：Yuan Wang、Junxian Yang、Xin Liu、Long Zhao、Dongxu Yang、Jingjing Zhou、Dan Wang、Lingyun Mou、Rui Wang

  DOI：10.1039/c7ob01115f

  日期：——

  This study describes the design and synthesis of endomorphin-1 analogs containing C-terminal aromatic α-methyl-β-amino acids and an N-terminal native tyrosine or 2,6-dimethyl-tyrosine. We show that, in comparison with the parent peptide, these analogs exhibit improved bioactivity and blood–brain barrier penetration after intravenous administration, and have a lower tendency to induce constipation and

  这项研究描述了含有C末端芳香族α-甲基-β-氨基酸和N末端天然酪氨酸或2,6-二甲基酪氨酸的内啡肽-1类似物的设计和合成。我们显示，与母体肽相比，这些类似物在静脉内给药后表现出更高的生物活性和血脑屏障渗透性，并且比吗啡具有更低的诱发便秘和镇静作用的趋势。