methyl (3S,4S)-3-O-formyl-4-(tert-butoxycarbonyl)amino-5-phenylpentanoate | 1350846-57-9

• 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: methyl (3S,4S)-3-O-formyl-4-(tert-butoxycarbonyl)amino-5-phenylpentanoate
• 英文别名: methyl (3S,4S)-3-formyloxy-4-[(2-methylpropan-2-yl)oxycarbonylamino]-5-phenylpentanoate
• CAS: 1350846-57-9
• 化学式: C₁₈H₂₅NO₆
• 分子量: 351.4
• InChiKey: GYPFZVSYBSKCAM-GJZGRUSLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  25
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  90.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl (3S,4S)-3-O-formyl-4-(tert-butoxycarbonyl)amino-5-phenylpentanoate 在 甲醇 、 水 、 对甲苯磺酸 、 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 2,4,5-三脱氧-4-[[(1,1-二甲基乙氧基)羰基]氨基]-5-苯基-L-苏-戊糖酸
  参考文献：
  名称：

  Stereodivergent approach to both syn- and anti-isomers of γ-amino-β-hydroxy acids: (3S,4S)- and (3R,4S)-AHPPA derivatives

  摘要：

  A stereodivergent approach employing an N-hydroxymethyl group has been utilized to produce both diastereomeric derivatives of (3S,4S)-AHPPA 3 and (312,4S)-AHPPA 4, via an intramolecular conjugate addition and an intramolecular epoxidation, respectively. The selectivity of the intramolecular conjugate addition was more than 10:1 while that of the intramolecular epoxidation was more than 1:20. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.09.021
• 作为产物：
  描述：

  在 叔丁基过氧化氢 、 ruthenium(III) trichloride hydrate 作用下， 以 癸烷 、 苯 为溶剂， 反应 7.0h， 以77%的产率得到methyl (3S,4S)-3-O-formyl-4-(tert-butoxycarbonyl)amino-5-phenylpentanoate
  参考文献：
  名称：

  Stereodivergent approach to both syn- and anti-isomers of γ-amino-β-hydroxy acids: (3S,4S)- and (3R,4S)-AHPPA derivatives

  摘要：

  A stereodivergent approach employing an N-hydroxymethyl group has been utilized to produce both diastereomeric derivatives of (3S,4S)-AHPPA 3 and (312,4S)-AHPPA 4, via an intramolecular conjugate addition and an intramolecular epoxidation, respectively. The selectivity of the intramolecular conjugate addition was more than 10:1 while that of the intramolecular epoxidation was more than 1:20. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.09.021

文献信息

• Stereodivergent approach to both syn- and anti-isomers of γ-amino-β-hydroxy acids: (3S,4S)- and (3R,4S)-AHPPA derivatives
  作者：Dongwon Yoo、Jeeyun Song、Moon Sung Kang、Eun-Sil Kang、Young Gyu Kim

  DOI：10.1016/j.tetasy.2011.09.021

  日期：2011.9

  A stereodivergent approach employing an N-hydroxymethyl group has been utilized to produce both diastereomeric derivatives of (3S,4S)-AHPPA 3 and (312,4S)-AHPPA 4, via an intramolecular conjugate addition and an intramolecular epoxidation, respectively. The selectivity of the intramolecular conjugate addition was more than 10:1 while that of the intramolecular epoxidation was more than 1:20. (C) 2011 Elsevier Ltd. All rights reserved.