(Allyloxycarbonyl)-(S)-3-<(1S,2R,3R)-2,3-epoxy-4-oxo-1-cyclohexyl>alanine methyl ester | 158109-60-5

• 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: (Allyloxycarbonyl)-(S)-3-<(1S,2R,3R)-2,3-epoxy-4-oxo-1-cyclohexyl>alanine methyl ester
• 英文别名: methyl (2S)-3-[(1R,2S,6R)-5-oxo-7-oxabicyclo[4.1.0]heptan-2-yl]-2-(prop-2-enoxycarbonylamino)propanoate
• CAS: 158109-60-5
• 化学式: C₁₄H₁₉NO₆
• 分子量: 297.308
• InChiKey: QUUMJVKDJZWYSM-XPXLGCRWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  94.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (Allyloxycarbonyl)-(S)-3-<(1S,2R,3R)-2,3-epoxy-4-oxo-1-cyclohexyl>alanine methyl ester 在 四(三苯基膦)钯 sodium hydroxide 、 N,N-二甲基三甲基硅胺 作用下， 生成 抗荚膜菌素
  参考文献：
  名称：

  Enantioselective Total Synthesis of the Antifungal Natural Products Chlorotetaine, Bacilysin, and Anticapsin and of Related Compounds: Revision of the Relative Configuration

  摘要：

  Enantioselective and diastereoselective syntheses of the title antifungal natural products and some of their diastereoisomers are described. Key steps include the diastereoselective 1,6-addition of bislactim ether 14 and a stereoselective, deprotonation of ketone 17 using lithium (S,S)-bis(1-phenylethyl)amide as a chiral base. All natural products possess the (S)-configuration at C-1 of the substituted cyclohex(en)yl residues of the C-terminal amino acids, which contradicts the assignments in the literature. At physiological pH most of the dipeptides are instable and react by an intramolecular 1,4-addition with the formation of 6-oxoperhydroindoles.

  DOI：

  10.1021/jo00089a019
• 作为产物：
  描述：

  (S)-2-Allyloxycarbonylamino-3-((S)-5-hydroxy-7-oxa-bicyclo[4.1.0]hept-2-yl)-propionic acid methyl ester 在 chromium trioxide-pyridine complex 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 生成 (Allyloxycarbonyl)-(S)-3-<(1S,2R,3R)-2,3-epoxy-4-oxo-1-cyclohexyl>alanine methyl ester 、 (Allyloxycarbonyl)-(S)-3-<(1S,2S,3S)-2,3-epoxy-4-oxo-1-cyclohexyl>alanine methyl ester
  参考文献：
  名称：

  Enantioselective Total Synthesis of the Antifungal Natural Products Chlorotetaine, Bacilysin, and Anticapsin and of Related Compounds: Revision of the Relative Configuration

  摘要：

  Enantioselective and diastereoselective syntheses of the title antifungal natural products and some of their diastereoisomers are described. Key steps include the diastereoselective 1,6-addition of bislactim ether 14 and a stereoselective, deprotonation of ketone 17 using lithium (S,S)-bis(1-phenylethyl)amide as a chiral base. All natural products possess the (S)-configuration at C-1 of the substituted cyclohex(en)yl residues of the C-terminal amino acids, which contradicts the assignments in the literature. At physiological pH most of the dipeptides are instable and react by an intramolecular 1,4-addition with the formation of 6-oxoperhydroindoles.

  DOI：

  10.1021/jo00089a019

文献信息

• Enantioselective Total Synthesis of the Antifungal Natural Products Chlorotetaine, Bacilysin, and Anticapsin and of Related Compounds: Revision of the Relative Configuration
  作者：Hanno Wild

  DOI：10.1021/jo00089a019

  日期：1994.5

  Enantioselective and diastereoselective syntheses of the title antifungal natural products and some of their diastereoisomers are described. Key steps include the diastereoselective 1,6-addition of bislactim ether 14 and a stereoselective, deprotonation of ketone 17 using lithium (S,S)-bis(1-phenylethyl)amide as a chiral base. All natural products possess the (S)-configuration at C-1 of the substituted cyclohex(en)yl residues of the C-terminal amino acids, which contradicts the assignments in the literature. At physiological pH most of the dipeptides are instable and react by an intramolecular 1,4-addition with the formation of 6-oxoperhydroindoles.