1-(tert-butyl-dimethyl-sylanyloxy)-2-deoxy-2-azido-3,4,6-tri-O-benzyl-5-oxo-D-glucitol | 765308-81-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(tert-butyl-dimethyl-sylanyloxy)-2-deoxy-2-azido-3,4,6-tri-O-benzyl-5-oxo-D-glucitol
• 英文别名: (3S,4R,5S)-5-azido-6-[tert-butyl(dimethyl)silyl]oxy-1,3,4-tris(phenylmethoxy)hexan-2-one
• CAS: 765308-81-4
• 化学式: C₃₃H₄₃N₃O₅Si
• 分子量: 589.807
• InChiKey: MHQYHXXKTWFYMJ-JIZBBPSKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.64
• 重原子数：
  42
• 可旋转键数：
  18
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  68.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-(tert-butyl-dimethyl-sylanyloxy)-2-deoxy-2-azido-3,4,6-tri-O-benzyl-5-oxo-D-glucitol 在 Lindlar's catalyst 氢气 、 sodium cyanoborohydride 、 对甲苯磺酸 作用下， 以 甲醇 、 甲苯 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 4.0h， 生成 (2S,3R,4R,5R)-2-(tert-butyl-dimethyl-sylanyloxy-methyl)-3,4-di-O-benzyl-5-(O-benzyl-methyl)-pyrrolidine
  参考文献：
  名称：

  Synthesis and High-Throughput Screening of N-Acetyl-β-hexosaminidase Inhibitor Libraries Targeting Osteoarthritis

  摘要：

  C1 Nitrogen iminocyclitols are potent inhibitors of N-acetyl-beta-hexosaminidases. Given hexosaminidases' important roles in osteoarthritis, we developed two straightforward and efficient syntheses of C1 nitrogen iminocyclitols from two readily available starting materials, D-mannosamine hydrochloride and the microbial oxidation product of fructose. A diversity-oriented synthetic strategy was then performed by coupling these core structures with various aldehydes, carboxylic acids, and alkynes to generate three separate libraries. High-throughput screening of the generated libraries with human N-acetyl-beta-hexosaminidases produced only moderate inhibitory activities. However, the synthetic approach and screening strategy for these compounds will be applied to develop new potent inhibitors of human N-acetyl-beta-hexosaminidases, particularly when combined with the structural information of these enzymes.

  DOI：

  10.1021/jo049355h
• 作为产物：
  描述：

  (2R,3R,4R,5S)-5-Azido-1,3,4-tris-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-hexan-2-ol 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 生成 1-(tert-butyl-dimethyl-sylanyloxy)-2-deoxy-2-azido-3,4,6-tri-O-benzyl-5-oxo-D-glucitol
  参考文献：
  名称：

  Synthesis and High-Throughput Screening of N-Acetyl-β-hexosaminidase Inhibitor Libraries Targeting Osteoarthritis

  摘要：

  C1 Nitrogen iminocyclitols are potent inhibitors of N-acetyl-beta-hexosaminidases. Given hexosaminidases' important roles in osteoarthritis, we developed two straightforward and efficient syntheses of C1 nitrogen iminocyclitols from two readily available starting materials, D-mannosamine hydrochloride and the microbial oxidation product of fructose. A diversity-oriented synthetic strategy was then performed by coupling these core structures with various aldehydes, carboxylic acids, and alkynes to generate three separate libraries. High-throughput screening of the generated libraries with human N-acetyl-beta-hexosaminidases produced only moderate inhibitory activities. However, the synthetic approach and screening strategy for these compounds will be applied to develop new potent inhibitors of human N-acetyl-beta-hexosaminidases, particularly when combined with the structural information of these enzymes.

  DOI：

  10.1021/jo049355h