5-azido-5-deoxy-1,2-O-isopropylidene-3,4-O-(o-xylylene)-β-D-fructopyranose | 1053612-41-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-azido-5-deoxy-1,2-O-isopropylidene-3,4-O-(o-xylylene)-β-D-fructopyranose
• 英文别名: (4S,4'R,4'aR,12'aS)-4'-azido-2,2-dimethylspiro[1,3-dioxolane-4,1'-3,4,4a,6,11,12a-hexahydropyrano[3,4-c][2,5]benzodioxocine]
• CAS: 1053612-41-1
• 化学式: C₁₇H₂₁N₃O₅
• 分子量: 347.371
• InChiKey: BCTWWVYIZPUJJE-AIANPOQGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  60.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5-azido-5-deoxy-1,2-O-isopropylidene-3,4-O-(o-xylylene)-β-D-fructopyranose 在 palladium on activated charcoal 盐酸 、 氢气 、 三氟乙酸 作用下， 以 甲醇 、 水 为溶剂， 20.0 ℃ 、400.0 kPa 条件下， 反应 24.5h， 生成 Alpha-葡萄糖苷酶
  参考文献：
  名称：

  Intramolecular Benzyl Protection Delivery:  A Practical Synthesis of DMDP and DGDP from d-Fructose

  摘要：

  A two-step protection of 1,2-diols as the corresponding o-xylylene cyclic ethers, involving an intramolecular ring-closing O-benzylation reaction, has been developed to overcome the problems associated to regioselective benzylation reactions. The strategy has been applied to the high-yielding synthesis of the pyrrolidine glycosidase inhibitors DMDP and DGDP.

  DOI：

  10.1021/ol052668u
• 作为产物：
  描述：

  1,2-二(溴甲基)苯 在 咪唑 、 六甲基磷酰三胺 、 sodium azide 、 碘 、 sodium hydride 、 溶剂黄146 、 三苯基膦 作用下， 以 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 54.58h， 生成 5-azido-5-deoxy-1,2-O-isopropylidene-3,4-O-(o-xylylene)-β-D-fructopyranose
  参考文献：
  名称：

  Intramolecular Benzyl Protection Delivery:  A Practical Synthesis of DMDP and DGDP from d-Fructose

  摘要：

  A two-step protection of 1,2-diols as the corresponding o-xylylene cyclic ethers, involving an intramolecular ring-closing O-benzylation reaction, has been developed to overcome the problems associated to regioselective benzylation reactions. The strategy has been applied to the high-yielding synthesis of the pyrrolidine glycosidase inhibitors DMDP and DGDP.

  DOI：

  10.1021/ol052668u

文献信息

• Intramolecular Benzyl Protection Delivery:  A Practical Synthesis of DMDP and DGDP from <scp>d</scp>-Fructose
  作者：M. Isabel García-Moreno、Matilde Aguilar、Carmen Ortiz Mellet、José M. García Fernández

  DOI：10.1021/ol052668u

  日期：2006.1.1

  A two-step protection of 1,2-diols as the corresponding o-xylylene cyclic ethers, involving an intramolecular ring-closing O-benzylation reaction, has been developed to overcome the problems associated to regioselective benzylation reactions. The strategy has been applied to the high-yielding synthesis of the pyrrolidine glycosidase inhibitors DMDP and DGDP.