(3,5-bisispropyloxy-4-methoxy-phenyl)-(2-hydroxy-1-phenyl-ethylamino)-acetonitrile | 171738-32-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (3,5-bisispropyloxy-4-methoxy-phenyl)-(2-hydroxy-1-phenyl-ethylamino)-acetonitrile
• 英文别名: (2R)-2-[[(1S)-2-hydroxy-1-phenylethyl]amino]-2-[4-methoxy-3,5-di(propan-2-yloxy)phenyl]acetonitrile
• CAS: 171738-32-2
• 化学式: C₂₃H₃₀N₂O₄
• 分子量: 398.502
• InChiKey: MDPJIGQBUJBVFH-VQTJNVASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  83.7
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3,5-bisispropyloxy-4-methoxy-phenyl)-(2-hydroxy-1-phenyl-ethylamino)-acetonitrile 在 盐酸 、 Pb(OAc) 、 水 、 碳酸氢钠 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 、 水 为溶剂， 反应 13.0h， 生成 prop-2-enyl (2R)-2-[4-methoxy-3,5-di(propan-2-yloxy)phenyl]-2-(2,2,2-trichloroethoxycarbonylamino)acetate
  参考文献：
  名称：

  Asymmetric synthesis of 3,5-bis(isopropyloxy)-4-methoxyphenyl glycine by way of a diastereoselective Strecker reaction and an Evans electrophilic amination reaction

  摘要：

  Two short syntheses of D-N-Boc-3,5-bis(isopropyloxy)-4-methoxyphenyl glycine, a central unit of vancomycin type antibiotics, have been developed. A diastereoselective Strecker reaction using (S)-phenylglycinol as a chiral inducer was the key step in the first synthesis, while Evans' electrophilic amination technology was employed for introducing both the amino function and the chirality in the second strategy. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00312-7
• 作为产物：
  描述：

  三甲基氰硅烷 、 L-苯甘氨醇 、 4-methoxy-3,5-diisopropyloxybenzaldehyde 以 甲醇 、 二氯甲烷 为溶剂， 以86%的产率得到(3,5-bisispropyloxy-4-methoxy-phenyl)-(2-hydroxy-1-phenyl-ethylamino)-acetonitrile
  参考文献：
  名称：

  Asymmetric synthesis of (2S,3R) β-(4-F-3-NO2) phenyl serine, D-(R)-4-methoxy-3,5-bistbutyldimethylsiloxy phenylglycine and their assemblage to C-O-D ring of vancomycin

  摘要：

  The asymmetric synthesis of two appropriately functionalized non-proteinogenic amino acids 2 and 3 needed for the total synthesis of vancomycin was described. The assemblage of these amino acids into linear tripeptide followed by biaryl ether formation via intramolecular SNAr reaction led to the fully functionalized C-O-D ring of vancomycin.

  DOI：

  10.1016/0040-4039(95)01409-b

文献信息

• Asymmetric synthesis of 3,5-bis(isopropyloxy)-4-methoxyphenyl glycine by way of a diastereoselective Strecker reaction and an Evans electrophilic amination reaction
  作者：Caroline Vergne、Jean-Philippe Bouillon、Jacqueline Chastanet、Michèle Bois-Choussy、Jieping Zhu

  DOI：10.1016/s0957-4166(98)00312-7

  日期：1998.9

  Two short syntheses of D-N-Boc-3,5-bis(isopropyloxy)-4-methoxyphenyl glycine, a central unit of vancomycin type antibiotics, have been developed. A diastereoselective Strecker reaction using (S)-phenylglycinol as a chiral inducer was the key step in the first synthesis, while Evans' electrophilic amination technology was employed for introducing both the amino function and the chirality in the second strategy. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Asymmetric synthesis of (2S,3R) β-(4-F-3-NO2) phenyl serine, D-(R)-4-methoxy-3,5-bistbutyldimethylsiloxy phenylglycine and their assemblage to C-O-D ring of vancomycin
  作者：Jieping Zhu、Jean-Philippe Bouillon、Girij Pal Singh、Jacqueline Chastanet、René Bengelmans

  DOI：10.1016/0040-4039(95)01409-b

  日期：1995.9

  The asymmetric synthesis of two appropriately functionalized non-proteinogenic amino acids 2 and 3 needed for the total synthesis of vancomycin was described. The assemblage of these amino acids into linear tripeptide followed by biaryl ether formation via intramolecular SNAr reaction led to the fully functionalized C-O-D ring of vancomycin.