6-<(tert-Butoxycarbonyl)amino>-1,5-imino-3,4-O-isopropylidene-1,5,6-trideoxy-D-mannitol | 172323-75-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-<(tert-Butoxycarbonyl)amino>-1,5-imino-3,4-O-isopropylidene-1,5,6-trideoxy-D-mannitol
• 英文别名: tert-butyl N-[[(3aR,4R,7R,7aR)-7-hydroxy-2,2-dimethyl-3a,4,5,6,7,7a-hexahydro-[1,3]dioxolo[4,5-c]pyridin-4-yl]methyl]carbamate
• CAS: 172323-75-0
• 化学式: C₁₄H₂₆N₂O₅
• 分子量: 302.371
• InChiKey: AQXGLEUPJMTOAZ-GWOFURMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  89
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6-<(tert-Butoxycarbonyl)amino>-1,5-imino-3,4-O-isopropylidene-1,5,6-trideoxy-D-mannitol 在 盐酸 、 (diethylamido)sulfur trifluoride 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 5.17h， 生成 6-Amino-2-fluoro-1,5-imino-1,2,5,6-tetradeoxy-D-glucitol dihydrochloride
  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：

  Methanesulfonic acid (S)-2-tert-butoxycarbonylamino-1-((4R,5S,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-ethyl ester 在 palladium on activated charcoal sodium azide 、 氢气 、 4-甲基苯磺酸吡啶 作用下， 以 甲醇 、 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 60.0~110.0 ℃ 、206.84 kPa 条件下， 反应 10.0h， 生成 6-<(tert-Butoxycarbonyl)amino>-1,5-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.