ethyl (2S)-2-[[(S)-tert-butylsulfinyl]amino]-3-(4-chlorophenyl)propanoate | 1416989-88-2

• 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: ethyl (2S)-2-[[(S)-tert-butylsulfinyl]amino]-3-(4-chlorophenyl)propanoate
• CAS: 1416989-88-2
• 化学式: C₁₅H₂₂ClNO₃S
• 分子量: 331.864
• InChiKey: OMEMXHAQQZPMDB-ZSEKCTLFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  21
• 可旋转键数：
  8
• 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：

  2-[(S)-叔丁基亚磺酰基]亚氨基乙酸乙酯 、 4-氯氯苄 在 magnesium 、 lithium chloride 、 zinc(II) chloride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以82%的产率得到ethyl (2S)-2-[[(S)-tert-butylsulfinyl]amino]-3-(4-chlorophenyl)propanoate
  参考文献：
  名称：

  Unnatural Chiral N-tert-Butanesulfinyl α-Amino Acid Synthesis; A General Synthetic Strategy to N-Boc-Phenylalanine Analogue Alternatives

  摘要：

  This work provides a general approach to unnatural chiral N-tert-butanesulfinyl alpha-amino acid synthesis with high yields and excellent diastereoselectivities (dr up to 98: 2). The asymmetric addition of organometallic reagents to N-tert-butylsulfinyl imino acetate proceeded with excellent diastereo- and regioselectivities even on a 10 mmol scale. The sterically constrained 2',6'-dimethyltyrosine (Dmt) derivative was also readily prepared from commercially available and inexpensive starting materials through simple steps.

  DOI：

  10.1055/s-0032-1317298

文献信息

• Unnatural Chiral N-tert-Butanesulfinyl α-Amino Acid Synthesis; A General Synthetic Strategy to N-Boc-Phenylalanine Analogue Alternatives
  作者：Rui Wang、Li Lin、Xu Fu、Xiaojuan Ma、Jinlong Zhang

  DOI：10.1055/s-0032-1317298

  日期：——

  This work provides a general approach to unnatural chiral N-tert-butanesulfinyl alpha-amino acid synthesis with high yields and excellent diastereoselectivities (dr up to 98: 2). The asymmetric addition of organometallic reagents to N-tert-butylsulfinyl imino acetate proceeded with excellent diastereo- and regioselectivities even on a 10 mmol scale. The sterically constrained 2',6'-dimethyltyrosine (Dmt) derivative was also readily prepared from commercially available and inexpensive starting materials through simple steps.