5-azido-5-deoxy-1,2-O-isopropylidene-6-O-triphenylmethyl-α-D-glucofuranose | 241148-72-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 5-azido-5-deoxy-1,2-O-isopropylidene-6-O-triphenylmethyl-α-D-glucofuranose
• CAS: 241148-72-1
• 化学式: C₂₈H₂₉N₃O₅
• 分子量: 487.555
• InChiKey: FCHSYWCHPREWJK-JQSCXEDISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.91
• 重原子数：
  36.0
• 可旋转键数：
  8.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  105.91
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  5-azido-5-deoxy-1,2-O-isopropylidene-6-O-triphenylmethyl-α-D-glucofuranose 在 palladium on activated charcoal sodium tetrahydroborate 、 3 A molecular sieve 、 Amberlite IR-120 (H+) 、 Amberlite IR-120(H+) 、 immobilised glucose isomerase 、 氢气 、 sodium acetate 、 magnesium sulfate 、 pyridinium chlorochromate 作用下， 以 甲醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 24.0h， 生成 (2S,3S,4R,5R)-2,5-bis(hydroxymethyl)pyrrolidine-3,4-diol
  参考文献：
  名称：

  Synthetic applications of glucose isomerase: isomerisation of C-5-modified (2R,3R,4R)-configured hexoses into the corresponding 2-ketoses

  摘要：

  Immobilised glucose isomerase (EC 5.3.1.5) accepted various (2R,3R,4R)-configured hexoses such as 5-deoxy-D-ribo-hexose, 5-azido-5-deoxy-D-allose, as well as the corresponding epimer at C-5, 5-azido-5-deoxy-L-talose, as substrates. From the resulting azidodeoxyketoses, 5-azido-5-deoxy-D-psico- and -L-tagatopyranose, the powerful D-galactosidase inhibitors 2,5-dideoxy-2,5-imino-D-galactital and -D-altritol were obtained in one additional step. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(99)00119-6
• 作为产物：
  描述：

  5-azido-5-deoxy-1,2-O-isopropylidene-α-D-glucuronolactone 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 生成 5-azido-5-deoxy-1,2-O-isopropylidene-6-O-triphenylmethyl-α-D-glucofuranose
  参考文献：
  名称：

  Binding and catalysis by yeast aldose reductase: A substrate-analog approach with new aldose derivatives

  摘要：

  5-Deoxy-D-xylofuranose derivatives and a range of new 5,6-dideoxy analogs of D-glucofuranose bearing azido or fluoro substituents were synthesised and employed as substrates of the NADH-dependent aldehyde reduction catalysed by yeast aldose reductase. In terms of catalytic efficiencies, these products proved to be superior to the parent compounds. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00255-3