{(R)-2-Amino-2-[(4R,5R)-5-((R)-1,2-dihydroxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-ethyl}-carbamic acid tert-butyl ester | 172323-81-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: {(R)-2-Amino-2-[(4R,5R)-5-((R)-1,2-dihydroxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-ethyl}-carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[(2R)-2-amino-2-[(4R,5R)-5-[(1R)-1,2-dihydroxyethyl]-2,2-dimethyl-1,3-dioxolan-4-yl]ethyl]carbamate
• CAS: 172323-81-8
• 化学式: C₁₄H₂₈N₂O₆
• 分子量: 320.386
• InChiKey: BEOZOYHFSAPVDS-GWOFURMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  123
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  {(R)-2-Amino-2-[(4R,5R)-5-((R)-1,2-dihydroxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-ethyl}-carbamic acid tert-butyl ester 以 甲醇 为溶剂， 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
• 作为产物：
  描述：

  1-[(tert-butoxycarbonyl)amino]-1-deoxy-3,4:5,6-di-O-isopropylidene-D-glucitol 在 palladium on activated charcoal 4-二甲氨基吡啶 、 sodium azide 、 氢气 、 4-甲基苯磺酸吡啶 、 三乙胺 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 25.0~110.0 ℃ 、206.84 kPa 条件下， 反应 10.17h， 生成 {(R)-2-Amino-2-[(4R,5R)-5-((R)-1,2-dihydroxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-ethyl}-carbamic acid tert-butyl ester
  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.