prop-2-enyl (2R)-2-amino-2-[4-methoxy-3,5-di(propan-2-yloxy)phenyl]acetate | 171738-34-4

• 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: prop-2-enyl (2R)-2-amino-2-[4-methoxy-3,5-di(propan-2-yloxy)phenyl]acetate
• CAS: 171738-34-4
• 化学式: C₁₈H₂₇NO₅
• 分子量: 337.416
• InChiKey: OOHFDCMNOPOSCZ-MRXNPFEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  80
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  prop-2-enyl (2R)-2-amino-2-[4-methoxy-3,5-di(propan-2-yloxy)phenyl]acetate 在 sodium tetrahydroborate 、 四(三苯基膦)钯 、 碳酸氢钠 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 2.17h， 生成 (2R)-2-[4-methoxy-3,5-di(propan-2-yloxy)phenyl]-2-(2,2,2-trichloroethoxycarbonylamino)acetic acid
  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：

  在 盐酸 、 Pb(OAc) 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 prop-2-enyl (2R)-2-amino-2-[4-methoxy-3,5-di(propan-2-yloxy)phenyl]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

文献信息

• 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.