(3aR,5R,6S,6aR)-5-[(1S)-2-amino-1-hydroxyethyl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-ol | 46417-66-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3aR,5R,6S,6aR)-5-[(1S)-2-amino-1-hydroxyethyl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-ol
• CAS: 46417-66-7
• 化学式: C₉H₁₇NO₅
• 分子量: 219.238
• InChiKey: VQSYZAHTGHBFKW-TVNFTVLESA-N

物化性质

• 沸点：
  420.0±40.0 °C(Predicted)
• 密度：
  1.302±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  94.2
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3aR,5R,6S,6aR)-5-[(1S)-2-amino-1-hydroxyethyl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-ol 在 palladium on activated charcoal 氢气 、 碳酸氢钠 、 三氟乙酸 作用下， 以 甲醇 、 水 为溶剂， 25.0 ℃ 、551.58 kPa 条件下， 反应 28.0h， 生成 1,6-dideoxy-1,6-imino-(2S,3R,4R,5S)-L-iditol
  参考文献：
  名称：

  Concise and practical synthesis of (2S,3R,4R,5R) and (2S,3R,4R,5S)-1,6-dideoxy-1,6-iminosugars

  摘要：

  The syntheses of (2S,3R,4R,5R) and (2S,3R,4R,5S)-1,6-dideoxy-1,6 iminosugars 1a and 1b, respectively, from D-glucose are described. The key transformations in this reaction sequence include regio-selective epoxide ring opening with N-benzylamine followed by intramolecular reductive amination of amino-aldehyde. (C) 2003 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(03)00177-7
• 作为产物：
  描述：

  3-O-benzyl-6-deoxy-6-nitro-1,2-O-isopropylidene-α-D-glucofuranose 在 palladium on activated charcoal ammonium formate 作用下， 以 甲醇 为溶剂， 反应 0.67h， 生成 (3aR,5R,6S,6aR)-5-[(1S)-2-amino-1-hydroxyethyl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-ol
  参考文献：
  名称：

  Short and efficient synthesis of (2S,3R,4R,5R) and (2S,3R,4R,5S)-tetrahydroxyazepanes via the Henry reaction

  摘要：

  The Henry reaction with the easily available alpha-D-xylo-pentodialdose afforded a diastereomeric mixture of nitroaldoses with the alpha-D-gluco- and beta-L-ido-configuration, respectively, in good yield. When n-BuLi was used as the base, the reaction afforded the alpha-D-gluco-nitroaldose as the only product. The reduction of the nitro group in the alpha-D-gluco- and beta-L-ido-nitroaldoses, removal of the protecting groups and intramolecular reductive cyclo-amination afforded the corresponding (2S,3R,4R,5R) and (2S,3R,4R,5S) tetrahydroxyazepanes. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.02.007