methyl (2S,3S)-3-[(tert-butoxycarbonyl)amino]-2-fluoro-3-phenylpropanoate | 1236280-73-1

• 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-3-phenylpropanoate
• CAS: 1236280-73-1
• 化学式: C₁₅H₂₀FNO₄
• 分子量: 297.327
• InChiKey: AWVFSLBLEXFVGE-RYUDHWBXSA-N

反应信息

• 作为产物：
  描述：

  (r)-n-boc-3-苯基-beta-丙氨酸甲酯 在 lithium diisopropyl amide 、 N-氟代双苯磺酰胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.0h， 生成 methyl (2S,3S)-3-[(tert-butoxycarbonyl)amino]-2-fluoro-3-phenylpropanoate 、 methyl (2R,3S)-3-[(tert-butoxycarbonyl)amino]-2-fluoro-3-phenylpropanoate
  参考文献：
  名称：

  含氟β2-和β3-氨基酸：α-胰胰蛋白酶的合成与抑制

  摘要：

  描述了一系列α-氟化的β2-和β3-氨基酸衍生物的合成。在的α碳的立体选择性氟化的β ³ α-氨基酸是由去质子化与二异丙基氨基锂，接着用治疗取得Ñ -fluorobenzenesulfonimide。的β氟化² α-氨基酸中使用的手性辅助剂（4 - [R）-4-苄基-2-恶唑烷酮。发现α-氟代氨基酸及其非氟代前体竞争性地抑制α-胰凝乳蛋白酶。 β-氨基酸-氟化-晶体结构-α-胰凝乳蛋白酶-抑制剂

  DOI：

  10.1055/s-0029-1218743

文献信息

• A Study on the Diastereoselective Synthesis of<i>α</i>-Fluorinated<i>β</i>³-Amino Acids by<i>α</i>-Fluorination
  作者：Victoria Peddie、Andrew D. Abell

  DOI：10.1002/hlca.201200520

  日期：2012.12

  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.