Benzyl N-(tert-butyloxycarbonyl)-O-benzyl-(S)-serinehydroxamate | 79722-11-5

• 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: Benzyl N-(tert-butyloxycarbonyl)-O-benzyl-(S)-serinehydroxamate
• 英文别名: Benzyl-N-(tert-butyloxycarbonyl)-O-benzyl-(S)-serinehydroxamate；N-Boc-O-Bzl-L-Ser-NHOBzl；(L)-N-α-Boc-serinyl-3-(O-benzyl)-1-O-benzylhydroxamate；tert-butyl N-[(2S)-1-oxo-3-phenylmethoxy-1-(phenylmethoxyamino)propan-2-yl]carbamate
• CAS: 79722-11-5
• 化学式: C₂₂H₂₈N₂O₅
• 分子量: 400.475
• InChiKey: OJBZQXPJUGBCSB-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  29
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  85.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Benzyl N-(tert-butyloxycarbonyl)-O-benzyl-(S)-serinehydroxamate 在 palladium on activated charcoal potassium tert-butylate 、 氢气 作用下， 以 甲醇 、 苯 为溶剂， 反应 167.0h， 生成 N-(tert-Butyloxycarbonyl)-(S)-norneoenactin A
  参考文献：
  名称：

  Synthesis of the antifungal agent norneoenactin A

  摘要：

  The first total and unequivocal syntheses of (R)- and (S)-norneoenactin A (1), an analog of the antifungal antibiotic neoenactin A, are described. The key step of each synthesis was the Michael addition of a serinehydroxamate (5 or 8) to the appropriate vinyl ketone 4. Biological activity of the two enantiomers of norneoenactin A ((S)-1 and (R)-1) against Escherichia coli and several fungi has been investigated.

  DOI：

  10.1021/jo00074a038
• 作为产物：
  描述：

  N-BOC-O-苄基-L-丝氨酸 、 苄氧基胺盐酸盐 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以89%的产率得到Benzyl N-(tert-butyloxycarbonyl)-O-benzyl-(S)-serinehydroxamate
  参考文献：
  名称：

  Synthesis of the antifungal agent norneoenactin A

  摘要：

  The first total and unequivocal syntheses of (R)- and (S)-norneoenactin A (1), an analog of the antifungal antibiotic neoenactin A, are described. The key step of each synthesis was the Michael addition of a serinehydroxamate (5 or 8) to the appropriate vinyl ketone 4. Biological activity of the two enantiomers of norneoenactin A ((S)-1 and (R)-1) against Escherichia coli and several fungi has been investigated.

  DOI：

  10.1021/jo00074a038

文献信息

• Synthesis and structure confirmation of fuscachelins A and B, structurally unique natural product siderophores from Thermobifida fusca
  作者：Eric J. Dimise、Heather L. Condurso、Geoffrey E. Stoker、Steven D. Bruner

  DOI：10.1039/c2ob26010g

  日期：——

  The fuscachelin siderophores have been prepared synthetically as have their metal chelation complexes. The heterodimeric nature of the fuscachelin decamer lends itself to a convergent synthetic strategy. Synthetic access to the natural products and intermediates will provide readily adaptable tools in future studies examining iron-sequestration and the biosynthetic machinery.

  富斯卡林铁载体及其金属螯合配合物已通过合成方法制备。fuscachelin decamer的异二聚体性质使其趋于融合的合成策略。合成获得的天然产物和中间体将为今后研究铁螯合和生物合成机制的研究提供容易适应的工具。
• N-Methylation of O-benzyl-.alpha.-N-(alkoxycarbonyl)-.alpha.-amino acid hydroxamate derivatives
  作者：K. Ramasamy、Richard K. Olsen、Thomas Emery

  DOI：10.1021/jo00339a047

  日期：1981.12
• Synthesis of the Antifungal Agent Neoenactin A and Its N-Deshydroxy Derivative
  作者：Ihab S. Darwish、Marvin J. Miller

  DOI：10.1021/jo00081a027

  日期：1994.1

  The first total and unequivocal syntheses of neoenactin A (1, NE A) as well as its N-deshydroxy analog 2 are described. The two key steps in the syntheses were the oxidative cleavage of an appropriate olefin 8a to yield the desired keto acid 9 and the Michael addition of serinehydroxamates 11 or 12 to the appropriate vinyl ketone 10. Biological activity of 1 and 2 against Escherichia coli and several fungi has been investigated.
• Synthesis of the antifungal agent norneoenactin A
  作者：Ihab S. Darwish、Chetna Patel、Marvin J. Miller

  DOI：10.1021/jo00074a038

  日期：1993.10

  The first total and unequivocal syntheses of (R)- and (S)-norneoenactin A (1), an analog of the antifungal antibiotic neoenactin A, are described. The key step of each synthesis was the Michael addition of a serinehydroxamate (5 or 8) to the appropriate vinyl ketone 4. Biological activity of the two enantiomers of norneoenactin A ((S)-1 and (R)-1) against Escherichia coli and several fungi has been investigated.