methyl 2,5-anhydro-6-deoxy-6-azido-D-mannonate | 222309-33-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,5-anhydro-6-deoxy-6-azido-D-mannonate
• 英文别名: methyl (2S,3S,4S,5R)-5-(azidomethyl)-3,4-dihydroxyoxolane-2-carboxylate
• CAS: 222309-33-3
• 化学式: C₇H₁₁N₃O₅
• 分子量: 217.181
• InChiKey: RUVRDQHMXBWCLJ-ZXXMMSQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  90.4
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 2,5-anhydro-6-deoxy-6-azido-D-mannonate 在 钯 氢气 、 potassium carbonate 作用下， 以 异丙醇 为溶剂， 生成 isopropyl 2,5-anhydro-6-amino-6-deoxy-D-mannonate
  参考文献：
  名称：

  Absence of secondary structure in a carbopeptoid tetramer of a trans-5-aminomethyl-tetrahydrofuran-2-carboxylate

  摘要：

  Whereas trimers and tetramers of beta-C-D-arabinofuranosyl carbohydrate amino acids adopt well defined conformations based around a repealing beta-turn like structure, stabilised by (i, i-2) inter-residue hydrogen bonds, there is no indication of any secondary structure in the tetramer of the epimeric alpha-C-D-arabinoluranosyl carbohydrate amino acid, where the C-2 and C-5 substituents of the tetrahydrofuran ring are Irans to each other. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00109-4
• 作为产物：
  描述：

  methyl 3,4:5,6-di-O-isopropylidene-D-gluconate 在 吡啶 、 盐酸 、 4-二甲氨基吡啶 、 sodium azide 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 40.75h， 生成 methyl 2,5-anhydro-6-deoxy-6-azido-D-mannonate
  参考文献：
  名称：

  Complex tetrahydrofurans from carbohydrate lactones: THF amino acids as building blocks for unnatural biopolymers

  摘要：

  文中介绍了基于 D-阿拉伯呋喃糖模板的两种六碳四氢呋喃羧酸表聚物的多克合成方法。此外，还详细介绍了 3-O-苄基保护衍生物的合成方法。在这些支架的 C-6 处引入氮，可生成适合于生成具有明确二级结构的低聚物的构建模块。自由基溴化促进了 C-2 位氮的引入，从而产生了同分异构的 α-氨基酸衍生物，这些衍生物被详细加工成两种非天然的非对映异构体，即强效除草天然产物 hydantocidin。此外，还披露了 N-甲基-2-叠氮-2-脱氧-α-D-阿拉伯-六-2-呋喃肌苷酰胺和 N-十二烷基-2-叠氮-2-脱氧-β-D-阿拉伯-六-2-呋喃肌苷酰胺的 X 射线晶体结构。

  DOI：

  10.1039/b111258a

文献信息

• Bend ribbon-forming tetrahydrofuran amino acidsThis is one of a number of contributions from the current members of the Dyson Perrins Laboratory to mark the end of almost 90 years of organic chemistry research in that building, as all its current academic staff move across South Parks Road to a new purpose-built laboratory.
  作者：Martin D. Smith、Timothy D. W. Claridge、Mark S. P. Sansom、George W. J. Fleet

  DOI：10.1039/b307707c

  日期：——

  Short oligomeric chains of C-glycosyl β-D-arabinofuranose configured tetrahydrofuran amino acids (where the C-2 and C-5 substituents of the tetrahydrofuran ring are cis to each other) exhibit a well-defined repeating turn secondary structure stabilised by (i, i − 2) inter-residue hydrogen bonds. This is in contrast to the epimeric α-D-arabinofuranose oligomer (where the C-2 and C-5 substituents of the tetrahydrofuran ring are trans to each other) in which there is no indication of any secondary structure in solution.

  C-糖基 β-D-阿拉伯呋喃糖配置的四氢呋喃氨基酸的短寡聚链（其中四氢呋喃环的 C-2 和 C-5 取代基彼此顺式）表现出明确的重复转角二级结构，通过（i ， 我 − 2) 残基间氢键。这与差向异构 α-D-阿拉伯呋喃糖低聚物（其中四氢呋喃环的 C-2 和 C-5 取代基彼此互为反式）相反，后者在溶液中没有任何二级结构的迹象。
• Complex tetrahydrofurans from carbohydrate lactones: THF amino acids as building blocks for unnatural biopolymers
  作者：Daniel D. Long、Martin D. Smith、Angeles Martín、Joseph R. Wheatley、David G. Watkin、Mattaius Müller、George W. J. Fleet

  DOI：10.1039/b111258a

  日期：——

  The multi-gram syntheses of two epimeric six-carbon tetrahydrofurancarboxylates based upon a D-arabinofuranose template are described. An approach to 3-O-benzyl protected derivatives is also detailed. Introduction of nitrogen at C-6 of these scaffolds leads to the generation of building blocks suitable for the generation of oligomers which possess well defined secondary structures. Radical bromination facilitates introduction of nitrogen at C-2, to afford anomeric α-amino acid derivatives which are elaborated to two unnatural diastereomers of the potent herbicidal natural product hydantocidin. X-Ray crystal structures of N-methyl-2-azido-2-deoxy-α-D-arabino-hex-2-ulofuranosonamide and N-dodecyl-2-azido-2-deoxy-β-D-arabino-hex-2-ulofuranosonamide are also disclosed.

  文中介绍了基于 D-阿拉伯呋喃糖模板的两种六碳四氢呋喃羧酸表聚物的多克合成方法。此外，还详细介绍了 3-O-苄基保护衍生物的合成方法。在这些支架的 C-6 处引入氮，可生成适合于生成具有明确二级结构的低聚物的构建模块。自由基溴化促进了 C-2 位氮的引入，从而产生了同分异构的 α-氨基酸衍生物，这些衍生物被详细加工成两种非天然的非对映异构体，即强效除草天然产物 hydantocidin。此外，还披露了 N-甲基-2-叠氮-2-脱氧-α-D-阿拉伯-六-2-呋喃肌苷酰胺和 N-十二烷基-2-叠氮-2-脱氧-β-D-阿拉伯-六-2-呋喃肌苷酰胺的 X 射线晶体结构。
• Absence of secondary structure in a carbopeptoid tetramer of a trans-5-aminomethyl-tetrahydrofuran-2-carboxylate
  作者：Martin D. Smith、Daniel D. Long、Angeles Martín、Daniel G. Marquess、Timothy D.W. Claridge、George W.J. Fleet

  DOI：10.1016/s0040-4039(99)00109-4

  日期：1999.3

  Whereas trimers and tetramers of beta-C-D-arabinofuranosyl carbohydrate amino acids adopt well defined conformations based around a repealing beta-turn like structure, stabilised by (i, i-2) inter-residue hydrogen bonds, there is no indication of any secondary structure in the tetramer of the epimeric alpha-C-D-arabinoluranosyl carbohydrate amino acid, where the C-2 and C-5 substituents of the tetrahydrofuran ring are Irans to each other. (C) 1999 Elsevier Science Ltd. All rights reserved.