Acetic acid (1R,2S,3R,4R,5R)-4-azido-2-((2R,3S,4R,5S,6S)-3,4,5-triacetoxy-6-methyl-tetrahydro-thiopyran-2-yloxy)-6,8-dioxa-bicyclo[3.2.1]oct-3-yl ester | 186967-43-1

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: Acetic acid (1R,2S,3R,4R,5R)-4-azido-2-((2R,3S,4R,5S,6S)-3,4,5-triacetoxy-6-methyl-tetrahydro-thiopyran-2-yloxy)-6,8-dioxa-bicyclo[3.2.1]oct-3-yl ester
• CAS: 186967-43-1
• 化学式: C₂₀H₂₇N₃O₁₁S
• 分子量: 517.514
• InChiKey: VTILRKBBGBXDNQ-UFJQVPECSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.99
• 重原子数：
  35.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  181.65
• 氢给体数：
  0.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (1R,2S,3R,4R,5R)-4-azido-2-((2R,3S,4R,5S,6S)-3,4,5-triacetoxy-6-methyl-tetrahydro-thiopyran-2-yloxy)-6,8-dioxa-bicyclo[3.2.1]oct-3-yl ester 在 吡啶 、 硫化氢 、 氨 、 三氟乙酸 作用下， 以 甲醇 为溶剂， 生成 5-thio-Fuc(a1-4)GlcNAc
  参考文献：
  名称：

  Synthesis of 5-Thio-l-fucose-Containing Disaccharides, as Sequence-Specific Inhibitors, and 2‘-Fucosyllactose, as a Substrate of α-l-Fucosidases

  摘要：

  Four 5-thio-L-fucose-containing disaccharides having alpha(1-->6), alpha(1-->3), alpha(1-->4)GlcNAc, and alpha(1-->2-Gal linkages (compounds 1-4, respectively) were synthesized as potential alpha-L-fucosidase inhibitors. The glycosylation reactions using 2,3,4-tri-O-acetyl-5-thio-L-fucopyranosyl trichloroacetimidate as a glycosyl donor and BF3 . OEt(2) as a catalyst gave mainly alpha-linked disaccharides. Only alpha(1-->2)-linked disaccharide 4 showed inhibitory activity (K-i = 0.21 mM) against Bacillus alpha-L-fucosidase which hydrolyzes the Fuc alpha(1-->2) linkage specifically. The results suggested that sequence specificity of an enzyme could be estimated from the inhibitory activities of the compounds 1-4. In contrast, every disaccharide showed inhibitory activity (K-i = 30-91 mu M) against bovine epididymis alpha-L-fucosidase.

  DOI：

  10.1021/jo961725h
• 作为产物：
  描述：

  在 三氟化硼乙醚 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 Acetic acid (1R,2S,3R,4R,5R)-4-azido-2-((2R,3S,4R,5S,6S)-3,4,5-triacetoxy-6-methyl-tetrahydro-thiopyran-2-yloxy)-6,8-dioxa-bicyclo[3.2.1]oct-3-yl ester
  参考文献：
  名称：

  Synthesis of 5-Thio-l-fucose-Containing Disaccharides, as Sequence-Specific Inhibitors, and 2‘-Fucosyllactose, as a Substrate of α-l-Fucosidases

  摘要：

  Four 5-thio-L-fucose-containing disaccharides having alpha(1-->6), alpha(1-->3), alpha(1-->4)GlcNAc, and alpha(1-->2-Gal linkages (compounds 1-4, respectively) were synthesized as potential alpha-L-fucosidase inhibitors. The glycosylation reactions using 2,3,4-tri-O-acetyl-5-thio-L-fucopyranosyl trichloroacetimidate as a glycosyl donor and BF3 . OEt(2) as a catalyst gave mainly alpha-linked disaccharides. Only alpha(1-->2)-linked disaccharide 4 showed inhibitory activity (K-i = 0.21 mM) against Bacillus alpha-L-fucosidase which hydrolyzes the Fuc alpha(1-->2) linkage specifically. The results suggested that sequence specificity of an enzyme could be estimated from the inhibitory activities of the compounds 1-4. In contrast, every disaccharide showed inhibitory activity (K-i = 30-91 mu M) against bovine epididymis alpha-L-fucosidase.

  DOI：

  10.1021/jo961725h