{4-Methoxy-3,5-bis[(propan-2-yl)oxy]phenyl}methanol | 918446-55-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: {4-Methoxy-3,5-bis[(propan-2-yl)oxy]phenyl}methanol
• 英文别名: [4-methoxy-3,5-di(propan-2-yloxy)phenyl]methanol
• CAS: 918446-55-6
• 化学式: C₁₄H₂₂O₄
• 分子量: 254.326
• InChiKey: IMQCWZRHBNLTLB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  {4-Methoxy-3,5-bis[(propan-2-yl)oxy]phenyl}methanol 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 生成 4-methoxy-3,5-diisopropyloxybenzaldehyde
  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
• 作为产物：
  描述：

  4-methoxy-3,5-diisopropyloxybenzaldehyde 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 以92%的产率得到{4-Methoxy-3,5-bis[(propan-2-yl)oxy]phenyl}methanol
  参考文献：
  名称：

  Synthesis of a model bicyclic C-O-D-O-E ring of vancomycin by a one-pot, double SNAr based macrocyclization

  摘要：

  在–5 °C下，使用CsF处理线性五肽3于DMF中，以一步法的方式得到万古霉素的模型双环CODOE环2。

  DOI：

  10.1039/cc9960001029

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.
• Synthesis of a model bicyclic C-O-D-O-E ring of vancomycin by a one-pot, double SNAr based macrocyclization
  作者：Ren� Beugelmans、Mich�le Bois-Choussy、Caroline Vergne、Jean-Philippe Bouillon、Jieping Zhu

  DOI：10.1039/cc9960001029

  日期：——

  Double cyclization of linear pentapeptide 3 by treatment with CsF in DMF at –5 °C gives a model bicyclic CODOE ring 2 of vancomycin in a one-pot fashion.

  在–5 °C下，使用CsF处理线性五肽3于DMF中，以一步法的方式得到万古霉素的模型双环CODOE环2。