ethyl (2R,3R)-3-azido-2-hydroxy-3-mesitylpropanoate | 1005385-66-9

• 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: ethyl (2R,3R)-3-azido-2-hydroxy-3-mesitylpropanoate
• 英文别名: ethyl (2R,3R)-3-azido-2-hydroxy-3-(2,4,6-trimethylphenyl)propanoate
• CAS: 1005385-66-9
• 化学式: C₁₄H₁₉N₃O₃
• 分子量: 277.323
• InChiKey: FWGXAHPJDBRVRZ-CHWSQXEVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  60.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl (2R,3R)-3-azido-2-hydroxy-3-mesitylpropanoate 在 锂硼氢 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 以88%的产率得到(2R,3R)-3-azido-3-(2,4,6-trimethylphenyl)propane-1,2-diol
  参考文献：
  名称：

  A unified approach to mesityl amino acids based on Sharpless dihydroxylation

  摘要：

  Enantioselective syntheses of two mesityl (2,4,6-trimethylphenyl) amino acids are described. Starting from ethyl 3-mesityl-2-propenoate both enantiomeric dihydroxy esters 5 were prepared in excellent yield and enantiomeric purity (>99% ee) by Sharpless dihydroxylation. Each diol was converted into ethyl 3-azido-2-hydroxy-3-mesitylpropanoate 3 which is the common intermediate. Compound (2S,3S)-3 was transformed into Fmoc-D-mesitylglycine D-1 and Fmoc-L-mesitylalanine L-2 through two four-step-sequences. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.10.041
• 作为产物：
  描述：

  (4R,5S)-4-ethoxycarbonyl-5-mesityl-1,3,2-dioxathiolane 2-oxide 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 以78%的产率得到ethyl (2R,3R)-3-azido-2-hydroxy-3-mesitylpropanoate
  参考文献：
  名称：

  A unified approach to mesityl amino acids based on Sharpless dihydroxylation

  摘要：

  Enantioselective syntheses of two mesityl (2,4,6-trimethylphenyl) amino acids are described. Starting from ethyl 3-mesityl-2-propenoate both enantiomeric dihydroxy esters 5 were prepared in excellent yield and enantiomeric purity (>99% ee) by Sharpless dihydroxylation. Each diol was converted into ethyl 3-azido-2-hydroxy-3-mesitylpropanoate 3 which is the common intermediate. Compound (2S,3S)-3 was transformed into Fmoc-D-mesitylglycine D-1 and Fmoc-L-mesitylalanine L-2 through two four-step-sequences. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.10.041

文献信息

• METHOD FOR THE STEREOSELECTIVE PREPARATION OF AMINO ACID DERIVATIVES
  申请人：BCN Peptides, S.A.

  公开号：EP2213653B1

  公开（公告）日：2012-09-05
• US8791294B2
  申请人：——

  公开号：US8791294B2

  公开（公告）日：2014-07-29