methyl (2S,3S)-3-[(tert-butoxycarbonyl)amino]-2-fluoro-5-methylhexanoate | 1420965-39-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl (2S,3S)-3-[(tert-butoxycarbonyl)amino]-2-fluoro-5-methylhexanoate
• CAS: 1420965-39-4
• 化学式: C₁₃H₂₄FNO₄
• 分子量: 277.336
• InChiKey: ARSXXUJGWANALT-UWVGGRQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.44
• 重原子数：
  19.0
• 可旋转键数：
  5.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  64.63
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  Boc-(S)-β³-HLeu-OMe 在 正丁基锂 、 二异丙胺 、 N-氟代双苯磺酰胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 5.5h， 以86%的产率得到
  参考文献：
  名称：

  A Study on the Diastereoselective Synthesis ofα-Fluorinatedβ³-Amino Acids byα-Fluorination

  摘要：

  AbstractThe treatment of a β3‐amino acid methyl ester with 2.2 equiv. of lithium diisopropylamide (LDA), followed by reaction with 5 equiv. of N‐fluorobenzenesulfonimide (NFSI) at −78° for 2.5 h and then 2 h at 0°, gives syn‐fluorination with high diastereoisomeric excess (de). The de and yield in these reactions are somewhat influenced by both the size of the amino acid side chain and the nature of the amine protecting group. In particular, fluorination of N‐Boc‐protected β3‐homophenylalanine, β3‐homoleucine, β3‐homovaline, and β3‐homoalanine methyl esters, 5 and 9–11, respectively, all proceeded with high de (>86% of the syn‐isomer). However, fluorination of N‐Boc‐protected β3‐homophenylglycine methyl ester (16) occurred with a significantly reduced de. The use of a Cbz or Bz amine‐protecting group (see 3 and 15) did not improve the de of fluorination. However, an N‐Ac protecting group (see 17) gave a reduced de of 26%. Thus, a large N‐protecting group should be employed in order to maximize selectivity for the syn‐isomer in these fluorination reactions.

  DOI：

  10.1002/hlca.201200520