6-deoxy-6-N-phenylmethylamino-1,2-O-isopropylidene-3-O-phenylmethyl-β-L-ido-1,4-furanose | 551960-78-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 6-deoxy-6-N-phenylmethylamino-1,2-O-isopropylidene-3-O-phenylmethyl-β-L-ido-1,4-furanose
• 英文别名: (1S)-1-[(3aR,5R,6S,6aR)-2,2-dimethyl-6-phenylmethoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-(benzylamino)ethanol
• CAS: 551960-78-2
• 化学式: C₂₃H₂₉NO₅
• 分子量: 399.487
• InChiKey: CKZLWFSCYDUTPV-MLBCHFTJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  69.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6-deoxy-6-N-phenylmethylamino-1,2-O-isopropylidene-3-O-phenylmethyl-β-L-ido-1,4-furanose 在 palladium on activated charcoal ammonium formate 、 碳酸氢钠 作用下， 以 甲醇 为溶剂， 反应 2.67h， 生成 6-deoxy-6-N-benzyloxycarbonyl-1,2-O-isopropylidene-3-O-phenylmethyl-β-L-ido-1,4-furanose
  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-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hex-5-enofuranose 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 41.0h， 生成 6-deoxy-6-N-phenylmethylamino-1,2-O-isopropylidene-3-O-phenylmethyl-β-L-ido-1,4-furanose
  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

文献信息

• Concise and practical synthesis of (2S,3R,4R,5R) and (2S,3R,4R,5S)-1,6-dideoxy-1,6-iminosugars
  作者：Jayant N Tilekar、Nitin T Patil、Harishchandra S Jadhav、Dilip D Dhavale

  DOI：10.1016/s0040-4020(03)00177-7

  日期：2003.3

  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.