isopropyl 6-amino-2,5-anhydro-6-deoxy-6-N-(2,5-anhydro-6-azido-6-deoxy-D-mannonyl)-D-mannonate | 222309-40-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: isopropyl 6-amino-2,5-anhydro-6-deoxy-6-N-(2,5-anhydro-6-azido-6-deoxy-D-mannonyl)-D-mannonate
• 英文别名: propan-2-yl (2S,3S,4S,5R)-5-[[[(2S,3S,4S,5R)-5-(azidomethyl)-3,4-dihydroxyoxolane-2-carbonyl]amino]methyl]-3,4-dihydroxyoxolane-2-carboxylate
• CAS: 222309-40-2
• 化学式: C₁₅H₂₄N₄O₉
• 分子量: 404.377
• InChiKey: CWFHNTPRHRDEOZ-FJLIWUEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  169
• 氢给体数：
  5
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  isopropyl 6-amino-2,5-anhydro-6-deoxy-6-N-(2,5-anhydro-6-azido-6-deoxy-D-mannonyl)-D-mannonate 在 sodium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.17h， 生成 6-amino-2,5-anhydro-6-deoxy-6-N-(2,5-anhydro-6-azido-6-deoxy-D-mannonyl)-D-mannonic acid
  参考文献：
  名称：

  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.

  摘要：

  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。

  DOI：

  10.1039/b307707c
• 作为产物：
  描述：

  methyl 2,5-anhydro-6-deoxy-6-azido-D-mannonate 在 sodium hydroxide 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.17h， 生成 isopropyl 6-amino-2,5-anhydro-6-deoxy-6-N-(2,5-anhydro-6-azido-6-deoxy-D-mannonyl)-D-mannonate
  参考文献：
  名称：

  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.

  摘要：

  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。

  DOI：

  10.1039/b307707c

文献信息

• 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.
• 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。