6-<(tert-Butoxycarbonyl)amino>-1,5-<(tert-butoxycarbonyl)imino>-3,4-O-isopropylidene-1,5,6-trideoxy-D-mannitol | 172323-83-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 6-<(tert-Butoxycarbonyl)amino>-1,5-<(tert-butoxycarbonyl)imino>-3,4-O-isopropylidene-1,5,6-trideoxy-D-mannitol
• 英文别名: tert-butyl (3aR,4R,7R,7aR)-7-hydroxy-2,2-dimethyl-4-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyridine-5-carboxylate
• CAS: 172323-83-0
• 化学式: C₁₉H₃₄N₂O₇
• 分子量: 402.488
• InChiKey: VVVHQGSPWQSBFE-AAVRWANBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  107
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  6-<(tert-Butoxycarbonyl)amino>-1,5-<(tert-butoxycarbonyl)imino>-3,4-O-isopropylidene-1,5,6-trideoxy-D-mannitol 在 4-二甲氨基吡啶 、 sodium azide 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.17h， 生成 2-Azido-6-<(tert-butoxycarbonyl)amino>-1,5-<(tert-butoxycarbonyl)imino>-3,4-O-isopropylidene-1,2,5,6-tetradeoxy-D-glucitol
  参考文献：
  名称：

  Synthesis of 2-azido-6-amino and 2-fluoro-6-amino analogs of 1-deoxynojirimycin

  摘要：

  1-Aminoglucitol (3) was transformed into iminosugars 5-8, piperidine analogues of manno- ana glucopyranose, by using a reversed-chain strategy in which the 1-amino group of 3 is retained as the 6-substituent of the iminosugars and the ring nitrogen is derived fi om an azido group introduced at C-2 of the N-Boc-3,4:5,6-O-diisopropylidene protected derivative 9. Successive deprotection of the 5,6-diol moiety, reduction of the azido group, and displacement of 6-OH with a bromo substituent result in generation of the iminosugar synthon 4. This can be deprotected directly or following inversion at the C-2 position to afford 6-amino-1,6-dideoxymannojirimycin (5) or 2-azido- and, 2-fluoro-6-amino-1,6-dideoxynojirimycin 7 and 8.

  DOI：

  10.1021/jo00123a017
• 作为产物：
  描述：

  2-Azido-1-<(tert-butoxycarbonyl)amino>-3,4-O-isopropylidene-1,2-dideoxy-D-mannitol 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 乙醇 为溶剂， 25.0 ℃ 、206.84 kPa 条件下， 反应 4.0h， 生成 6-<(tert-Butoxycarbonyl)amino>-1,5-<(tert-butoxycarbonyl)imino>-3,4-O-isopropylidene-1,5,6-trideoxy-D-mannitol
  参考文献：
  名称：

  Synthesis of 2-azido-6-amino and 2-fluoro-6-amino analogs of 1-deoxynojirimycin

  摘要：

  1-Aminoglucitol (3) was transformed into iminosugars 5-8, piperidine analogues of manno- ana glucopyranose, by using a reversed-chain strategy in which the 1-amino group of 3 is retained as the 6-substituent of the iminosugars and the ring nitrogen is derived fi om an azido group introduced at C-2 of the N-Boc-3,4:5,6-O-diisopropylidene protected derivative 9. Successive deprotection of the 5,6-diol moiety, reduction of the azido group, and displacement of 6-OH with a bromo substituent result in generation of the iminosugar synthon 4. This can be deprotected directly or following inversion at the C-2 position to afford 6-amino-1,6-dideoxymannojirimycin (5) or 2-azido- and, 2-fluoro-6-amino-1,6-dideoxynojirimycin 7 and 8.

  DOI：

  10.1021/jo00123a017

文献信息

• Synthesis of 2-azido-6-amino and 2-fluoro-6-amino analogs of 1-deoxynojirimycin
  作者：Amuri Kilonda、Frans Compernolle、Georges J. Hoornaert

  DOI：10.1021/jo00123a017

  日期：1995.9

  1-Aminoglucitol (3) was transformed into iminosugars 5-8, piperidine analogues of manno- ana glucopyranose, by using a reversed-chain strategy in which the 1-amino group of 3 is retained as the 6-substituent of the iminosugars and the ring nitrogen is derived fi om an azido group introduced at C-2 of the N-Boc-3,4:5,6-O-diisopropylidene protected derivative 9. Successive deprotection of the 5,6-diol moiety, reduction of the azido group, and displacement of 6-OH with a bromo substituent result in generation of the iminosugar synthon 4. This can be deprotected directly or following inversion at the C-2 position to afford 6-amino-1,6-dideoxymannojirimycin (5) or 2-azido- and, 2-fluoro-6-amino-1,6-dideoxynojirimycin 7 and 8.