<2(S,R),3(S,R),4(S,R)>-2-amino-4-hydroxy-4-(4-methoxyphenyl)-3-methylbutanoic acid | 88155-33-3

• 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: <2(S,R),3(S,R),4(S,R)>-2-amino-4-hydroxy-4-(4-methoxyphenyl)-3-methylbutanoic acid
• CAS: 88155-33-3
• 化学式: C₁₂H₁₇NO₄
• 分子量: 239.271
• InChiKey: DLJPLKRVJKSOIJ-AVPPRXQKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.78
• 重原子数：
  17.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  92.78
• 氢给体数：
  3.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  <2(S,R),3(S,R),4(S,R)>-2-amino-4-hydroxy-4-(4-methoxyphenyl)-3-methylbutanoic acid 在 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 0.08h， 生成 <3(S,R),4(S,R),5(S,R)>-3-amino-5-(4-methoxyphenyl)-4-methyltetrahydrofuran-2-one hydrogen 4-toluenesulfonate
  参考文献：
  名称：

  .alpha.-Oximino amide trianions in the stereoselective synthesis of isoxazolines and .gamma.-hydroxy .alpha.-amino acids

  摘要：

  The trianions 17 and 33, which were prepared from the corresponding alpha-oximino amides 7 and 30, were reacted with 4-methoxybenzaldehyde to stereoselectively provide, on acidification, the corresponding trans-substituted isoxazoline-3-carboxamides 8 and 31/32, respectively. Additionally, the dianion 24, which was prepared from the corresponding O-silyl oxime 22, was reacted with 4-methoxybenzaldehyde to stereoselectively give the anti beta-hydroxy oxime 23. Reduction of 8 and 26 stereoselectively gave the 2,3-syn-3,4-anti amino amides 11 and 27. Amides 11 and 27 were subsequently converted to the gamma-hydroxy-alpha-amino acids 12 and 29 and the corresponding lactones 13 and 28. Amino acid 29 is the N-terminal amino acid of the antifungal agent nikkomycin B.

  DOI：

  10.1021/jo00005a042
• 作为产物：
  描述：

  <2(S,R),3(S,R),4(S,R)>-2-amino-4-hydroxy-4-(4-methoxyphenyl)-3-methyl-N-tert-butylbutanamide 在 三氟乙酸 作用下， 反应 18.0h， 生成 <2(S,R),3(S,R),4(S,R)>-2-amino-4-hydroxy-4-(4-methoxyphenyl)-3-methylbutanoic acid
  参考文献：
  名称：

  .alpha.-Oximino amide trianions in the stereoselective synthesis of isoxazolines and .gamma.-hydroxy .alpha.-amino acids

  摘要：

  The trianions 17 and 33, which were prepared from the corresponding alpha-oximino amides 7 and 30, were reacted with 4-methoxybenzaldehyde to stereoselectively provide, on acidification, the corresponding trans-substituted isoxazoline-3-carboxamides 8 and 31/32, respectively. Additionally, the dianion 24, which was prepared from the corresponding O-silyl oxime 22, was reacted with 4-methoxybenzaldehyde to stereoselectively give the anti beta-hydroxy oxime 23. Reduction of 8 and 26 stereoselectively gave the 2,3-syn-3,4-anti amino amides 11 and 27. Amides 11 and 27 were subsequently converted to the gamma-hydroxy-alpha-amino acids 12 and 29 and the corresponding lactones 13 and 28. Amino acid 29 is the N-terminal amino acid of the antifungal agent nikkomycin B.

  DOI：

  10.1021/jo00005a042

文献信息

• Synthese reiner Stereoisomerer der N-terminalen Aminosäure von Nikkomycin B
  作者：Gesine Zimmermann、Werner Hass、Holger Faasch、Helmut Schmalle、Wilfried A. König

  DOI：10.1002/jlac.198519851107

  日期：1985.11.12

  Reine Stereoisomere von 2-Amino-4-hydroxy-4-(p-hydroxyphenyl)-3-methylbuttersäure (8c), der N-terminalen Aminosäure von Nikkomycin B (10a, b), wurden nach 1,3-dipolarer Cycloaddition von (Ethoxycarbonyl)methannitriloxid (2) an die Olefine 1 und Trennung der diastereomeren 4,5-Dihydro-3-isoxazolcarboxamide 6 durch diastereoselektive reduktive Spaltung und Verseifung von 6 hergestellt. Mit Hilfe eines

  1,3-偶极后，获得了尼克霉素B（10a，b）的N末端氨基酸2-氨基-4-羟基-4-（对羟基苯基）-3-甲基丁酸（8c）的纯立体异构体。的环加成（乙氧羰基）methanenitrile氧化物（2）在烯烃1的非对映体4,5-二氢-3-异恶唑甲酰胺和分离6由非对映选择性还原裂解和皂化6。使用8c的纯合成立体异构体，其绝对构型（2 R，3 R，4 R）可以通过晶体结构分析确定，以及借助手性相的气相色谱法和1 H-NMR可以将构型（2 S，3 S，4 S）分配给天然氨基酸。
• Novel anionic reagents for the stereoselective synthesis of γ-hydroxy-α-amino-acids. An X-ray crystallographic study of 2R(S)-benzoylamino-N-t-butyl-4R(S)-hydroxy-4-(4-methoxyphenyl)-3R(S)-methylbutanamide
  作者：Bernard J. Banks、Anthony G. M. Barrett、Mark A. Russell、David J. Williams

  DOI：10.1039/c39830000873

  日期：——

  e2-But)CONHBut, prepared respectively from 4-methoxybenzaldehyde (ArCHO) and the anions MeCHC-(–)C(NBut) and MeCHC(–OSiMe2But)C(NBut), were reduced stereoselectively (25:1) and benzoylated to produce the title amide which was characterized by an X-ray analysis.

  异恶唑啉的反式-Ar [图形省略]）CONHBu吨和肟苏-ARCH（OH）CH（Me）的C（NOSiMe 2 -Bu吨）CONHBu吨，由4-甲氧基苯甲醛（ArCHO）和阴离子分别机甲制备C-将（– ）C（NBu t）和MeCH C（–OSiMe 2 Bu t）C（NBu t）进行立体选择性还原（25：1）和苯甲酰化，生成标题酰胺，通过X射线分析对其进行表征。