N-(allyloxycarbonyl)-O-benzylhydroxylamine | 125049-89-0

• 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: N-(allyloxycarbonyl)-O-benzylhydroxylamine
• 英文别名: prop-2-enyl N-phenylmethoxycarbamate
• CAS: 125049-89-0
• 化学式: C₁₁H₁₃NO₃
• 分子量: 207.229
• InChiKey: HNZSGHUVAKJLCI-UHFFFAOYSA-N

物化性质

• 密度：
  1.116±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(allyloxycarbonyl)-O-benzylhydroxylamine 在 三苯基膦 、 三氟乙酸 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 14.0h， 生成 (2S)-2-(phenylmethoxycarbonylamino)-5-[phenylmethoxy(prop-2-enoxycarbonyl)amino]pentanoic acid
  参考文献：
  名称：

  Synthesis of foroxymithine, a microbial fermentation product and angiotensin 1 converting enzyme inhibitor

  摘要：

  The first total synthesis of the microbial fermentation product, ferric ion chelator and angiotensin converting enzyme inhibitor foroxymithine 1 is described. In addition to firmly establishing the reported structure of 1, a flexible synthetic strategy was employed which will allow the future syntheses of various derivatives and conjugates. Use of the chiral building block L-glutamic acid and conversion to the protected delta-hydroxynorvaline 3, followed by synthesis of the protected hydroxamic acids 4 and 5, afforded the precursor fragments needed. A series of peptide coupling reactions, including the problems encountered and conditions devised for the formation of the diketopiperazine 13 in good yield, are discussed. Finally, coupling of the left- and right-hand fragments, acetylation, deprotection, and hydrogenolysis gave foroxymithine 1.

  DOI：

  10.1021/jo00002a005
• 作为产物：
  描述：

  O-苄基羟胺 、 氯甲酸烯丙酯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以96%的产率得到N-(allyloxycarbonyl)-O-benzylhydroxylamine
  参考文献：
  名称：

  Synthesis of foroxymithine, a microbial fermentation product and angiotensin 1 converting enzyme inhibitor

  摘要：

  The first total synthesis of the microbial fermentation product, ferric ion chelator and angiotensin converting enzyme inhibitor foroxymithine 1 is described. In addition to firmly establishing the reported structure of 1, a flexible synthetic strategy was employed which will allow the future syntheses of various derivatives and conjugates. Use of the chiral building block L-glutamic acid and conversion to the protected delta-hydroxynorvaline 3, followed by synthesis of the protected hydroxamic acids 4 and 5, afforded the precursor fragments needed. A series of peptide coupling reactions, including the problems encountered and conditions devised for the formation of the diketopiperazine 13 in good yield, are discussed. Finally, coupling of the left- and right-hand fragments, acetylation, deprotection, and hydrogenolysis gave foroxymithine 1.

  DOI：

  10.1021/jo00002a005

文献信息

• A novel method for the formation of N-glycosides using hydroxamate
  作者：Jun Nakano、Tsuyoshi Ichiyanagi、Hiromichi Ohta、Yukishige Ito

  DOI：10.1016/s0040-4039(03)00473-8

  日期：2003.3

  nitrogen. We report here the novel N-glycosylation using Asn hydroxamate as a glycosyl acceptor. Reaction with glycosyl fluoride or glycosyl trichloroacetimidate afforded N-glycoside and subsequent reduction with SmI2 gave Asn-linked glucose. Carbamate derived hydroxamates proved to have even enhanced reactivity to give N-glycosides in high yields.

  由于缺乏羧酰胺氮的亲核性，难以通过N-糖基化直接形成Asn-连接的碳水化合物。我们在这里报告使用Asn异羟肟酸酯作为糖基受体的新型N-糖基化。与糖基氟化物或糖基三氯乙酰亚胺酸酯反应，得到N-糖苷，随后用SmI 2还原，得到Asn-连接的葡萄糖。氨基甲酸酯衍生的异羟肟酸酯经证实具有更高的反应活性，可以高收率得到N-糖苷。
• The Preparation of a Fully Differentiated “Multiwarhead” Siderophore Precursor
  作者：Aaron P. Murray、Marvin J. Miller

  DOI：10.1021/jo026391c

  日期：2003.1.1

  A protected, fully differentiated siderophore analogue has been prepared so that "Trojan Horse" -like siderophore drug conjugates with different drugs can be synthesized. The key steps in the synthesis include controlled preparation of an unsymmetrical urea and its conversion to a fully differentiated isocyanurate by reaction with chloro(carbonyl) isocyanate.