6-azido-3,6-dideoxy-D-xylo-hexono-1,4-lactone | 269741-55-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 6-azido-3,6-dideoxy-D-xylo-hexono-1,4-lactone
• 英文别名: (3R,5R)-5-[(1R)-2-azido-1-hydroxyethyl]-3-hydroxyoxolan-2-one
• CAS: 269741-55-1
• 化学式: C₆H₉N₃O₄
• 分子量: 187.155
• InChiKey: MCRKEFYDNVKAMY-UOWFLXDJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  81.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6-azido-3,6-dideoxy-D-xylo-hexono-1,4-lactone 在 palladium on activated charcoal 吡啶 、 氢气 作用下， 以 甲醇 为溶剂， 反应 12.25h， 生成 2,4,6-tri-O-acetyl-6-amino-3,6-dideoxy-D-xylo-hexono-1,6-lactam
  参考文献：
  名称：

  Synthesis and structure of 6-amino-2,3,6-trideoxy-d-erythro-hexono-1,6-lactam and 6-amino-3,6-dideoxy-d-xylo-hexono-1,6-lactam

  摘要：

  Solid-state conformations of 6-amino-2,3,6-trideoxy-D-erythro-hexono-1,6-lactam (3a) and 6-amino-3,6-dideoxy-D-xylo-hexono-1,6-lactam (7a) were determined using X-ray diffraction. Conformations of the compounds 3a, 7a, and their per-O-acetyl derivatives 4,5-di-O-acetyl-6-amino-2,3,6-trideoxy-D-erythro-hexono-1,6-lactam (3b) and 2,4,5-tri-O-acetyl-6-amino-3,6-dideoxy-D-xylo-hexono-1,6-lactam (7b) in solutions were deduced from the analysis of NMR spectra using a modified Karplus equation and compared with the results of circular dichroism measurement of lactams 3a and 7a. Conformation C-4(1,N) was revealed for solid lactams 3a and 7a and for lactams 7a and 7b in solution, while lactams 3a and 3b in solution exist in the similar to 1:1 equilibrium of the conformers C-4(1,N) and C-1,N(4). (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(99)00319-5
• 作为产物：
  描述：

  3-deoxy-1,2-O-isopropylidene-6-O-tosyl-α-D-xylo-hexofuranose 在 sodium azide 、 Dowex WX 4 resin 、 水 、 溴 、 barium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 2.25h， 生成 6-azido-3,6-dideoxy-D-xylo-hexono-1,4-lactone
  参考文献：
  名称：

  Synthesis and structure of 6-amino-2,3,6-trideoxy-d-erythro-hexono-1,6-lactam and 6-amino-3,6-dideoxy-d-xylo-hexono-1,6-lactam

  摘要：

  Solid-state conformations of 6-amino-2,3,6-trideoxy-D-erythro-hexono-1,6-lactam (3a) and 6-amino-3,6-dideoxy-D-xylo-hexono-1,6-lactam (7a) were determined using X-ray diffraction. Conformations of the compounds 3a, 7a, and their per-O-acetyl derivatives 4,5-di-O-acetyl-6-amino-2,3,6-trideoxy-D-erythro-hexono-1,6-lactam (3b) and 2,4,5-tri-O-acetyl-6-amino-3,6-dideoxy-D-xylo-hexono-1,6-lactam (7b) in solutions were deduced from the analysis of NMR spectra using a modified Karplus equation and compared with the results of circular dichroism measurement of lactams 3a and 7a. Conformation C-4(1,N) was revealed for solid lactams 3a and 7a and for lactams 7a and 7b in solution, while lactams 3a and 3b in solution exist in the similar to 1:1 equilibrium of the conformers C-4(1,N) and C-1,N(4). (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(99)00319-5

文献信息

• Synthesis and structure of 6-amino-2,3,6-trideoxy-d-erythro-hexono-1,6-lactam and 6-amino-3,6-dideoxy-d-xylo-hexono-1,6-lactam
  作者：Michaela Hamernı́ková、Svetlana Pakhomova、Jaroslav Havlı́ček、Hana Votavová、Karel Kefurt

  DOI：10.1016/s0008-6215(99)00319-5

  日期：2000.3

  Solid-state conformations of 6-amino-2,3,6-trideoxy-D-erythro-hexono-1,6-lactam (3a) and 6-amino-3,6-dideoxy-D-xylo-hexono-1,6-lactam (7a) were determined using X-ray diffraction. Conformations of the compounds 3a, 7a, and their per-O-acetyl derivatives 4,5-di-O-acetyl-6-amino-2,3,6-trideoxy-D-erythro-hexono-1,6-lactam (3b) and 2,4,5-tri-O-acetyl-6-amino-3,6-dideoxy-D-xylo-hexono-1,6-lactam (7b) in solutions were deduced from the analysis of NMR spectra using a modified Karplus equation and compared with the results of circular dichroism measurement of lactams 3a and 7a. Conformation C-4(1,N) was revealed for solid lactams 3a and 7a and for lactams 7a and 7b in solution, while lactams 3a and 3b in solution exist in the similar to 1:1 equilibrium of the conformers C-4(1,N) and C-1,N(4). (C) 2000 Elsevier Science Ltd. All rights reserved.