6-azido-3,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hexofuranose | 269741-53-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-azido-3,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hexofuranose
• 英文别名: (1R)-1-[(3aR,5R,6aR)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-azidoethanol
• CAS: 269741-53-9
• 化学式: C₉H₁₅N₃O₄
• 分子量: 229.236
• InChiKey: LVYLBTPCNMTJDG-WCTZXXKLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  62.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6-azido-3,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hexofuranose 在 Dowex WX 4 resin 、 水 、 溴 、 barium carbonate 作用下， 反应 1.75h， 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
• 作为产物：
  描述：

  5-(2,2-二甲基-1,3-二氧戊环-4-基)-2,2-二甲基四氢呋喃并[2,3-d][1,3]二氧杂环戊烯 在 sodium azide 、 溶剂黄146 作用下， 以 吡啶 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.0h， 生成 6-azido-3,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hexofuranose
  参考文献：
  名称：

  Syntheses of sugar-related trihydroxyazepanes from simple carbohydrates and their activities as reversible glycosidase inhibitors

  摘要：

  Five diastereomeric trideoxy-1,6-iminohexitols were synthesised, and their inhibitory activities were determined against selected glycosidases. For comparison, 1,4,5-trideoxy-l,5-imino-D-lyxo-hexitol, the 4-deoxy derivative of 1-deoxymannojirimicin, was prepared by enzymatic isomerisation of 6-azido-3,6-dideoxy-D-riho-hexose into the corresponding 2-ulose and subsequent hydrogenation accompanied by intramolecular reductive amination. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(00)00018-5

文献信息

• Syntheses of sugar-related trihydroxyazepanes from simple carbohydrates and their activities as reversible glycosidase inhibitors
  作者：Søren M Andersen、Christian Ekhart、Inge Lundt、Arnold E Stütz

  DOI：10.1016/s0008-6215(00)00018-5

  日期：2000.5

  Five diastereomeric trideoxy-1,6-iminohexitols were synthesised, and their inhibitory activities were determined against selected glycosidases. For comparison, 1,4,5-trideoxy-l,5-imino-D-lyxo-hexitol, the 4-deoxy derivative of 1-deoxymannojirimicin, was prepared by enzymatic isomerisation of 6-azido-3,6-dideoxy-D-riho-hexose into the corresponding 2-ulose and subsequent hydrogenation accompanied by intramolecular reductive amination. (C) 2000 Elsevier Science Ltd. All rights reserved.
• 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.