4-azido-4-deoxy-2,3:5,6-di-O-isopropylidene-D-galactose | 116087-62-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-azido-4-deoxy-2,3:5,6-di-O-isopropylidene-D-galactose
• 英文别名: (4R,5S)-5-[(S)-azido-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl]-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde
• CAS: 116087-62-8
• 化学式: C₁₂H₁₉N₃O₅
• 分子量: 285.3
• InChiKey: CYFJXNSDXKLFNO-QCLAVDOMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  68.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-azido-4-deoxy-2,3:5,6-di-O-isopropylidene-D-galactose 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 乙醇 为溶剂， 生成 1,4-dideoxy-1,4-imino-5-hydroxy-L-iditol
  参考文献：
  名称：

  New synthesis of 1,4-dideoxy-1,4-imino-d-galactitol from d-glucose propane-1,3-diyl dithioacetal

  摘要：

  The treatment of 4-azido-4-deoxy-2,3:5,6-di-O-isopropylidene-D-galactose propane-1,3-diyl dithioacetal (derived from D-glucose) with mercuric chloride and mercuric oxide in aqueous acetone afforded 4-azido-4-deoxy-2,3:5,6-di-O-isopropylidene-D-galactose. Acid-catalyzed deprotection of the azido derivative, followed by catalytic hydrogenation and concomitant intramolecular reductive amination in the presence of 10% palladium on carbon, gave 1,4-dideoxy-1,4-imino-D-galactitol in good yield. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(01)02167-0
• 作为产物：
  描述：

  D-glucose propane-1,3-diyl dithioacetal 在 sodium azide 、 四丁基溴化铵 、 对甲苯磺酸 、 尿素 、 mercury dichloride 、 mercury(II) oxide 作用下， 以 吡啶 、 乙二醇二甲醚 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 48.0h， 生成 4-azido-4-deoxy-2,3:5,6-di-O-isopropylidene-D-galactose
  参考文献：
  名称：

  New synthesis of 1,4-dideoxy-1,4-imino-d-galactitol from d-glucose propane-1,3-diyl dithioacetal

  摘要：

  The treatment of 4-azido-4-deoxy-2,3:5,6-di-O-isopropylidene-D-galactose propane-1,3-diyl dithioacetal (derived from D-glucose) with mercuric chloride and mercuric oxide in aqueous acetone afforded 4-azido-4-deoxy-2,3:5,6-di-O-isopropylidene-D-galactose. Acid-catalyzed deprotection of the azido derivative, followed by catalytic hydrogenation and concomitant intramolecular reductive amination in the presence of 10% palladium on carbon, gave 1,4-dideoxy-1,4-imino-D-galactitol in good yield. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(01)02167-0

文献信息

• Improved synthesis of 1,4-dideoxy-1,4-imino-d-galactitol, an inhibitor of E. coli K12 UDP-Gal mutase and mycobacterial galactan biosynthesis
  作者：Duy-Phong Pham-Huu、Yonas Gizaw、James N BeMiller、Ladislav Petruš

  DOI：10.1016/j.tet.2003.09.058

  日期：2003.11

  The E. Coli K12 UDP-Gal mutase inhibitor I was prepared from D-glucose in 5 steps (42% overall yield). The 4-azido galactose derivative 11, leading to 1, was formed by treatment of galactose dithioacetal 7 with mercuric oxide and mercuric chloride in acetone. To obtain 7. acetal 3 was tosylated or triflated and treated with NaN3. (C) 2003 Elsevier Ltd. All rights reserved.