Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-5-acetylamino-6-allyloxy-2-((2R,3S,4R,5S,6S)-3,4,5-triacetoxy-6-methyl-tetrahydro-thiopyran-2-yloxymethyl)-tetrahydro-pyran-4-yl ester | 186967-22-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-5-acetylamino-6-allyloxy-2-((2R,3S,4R,5S,6S)-3,4,5-triacetoxy-6-methyl-tetrahydro-thiopyran-2-yloxymethyl)-tetrahydro-pyran-4-yl ester
• CAS: 186967-22-6
• 化学式: C₂₇H₃₉NO₁₄S
• 分子量: 633.671
• InChiKey: STPCUZAFUGBEHU-XXBCGHMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.56
• 重原子数：
  43.0
• 可旋转键数：
  12.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  188.29
• 氢给体数：
  1.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-5-acetylamino-6-allyloxy-2-((2R,3S,4R,5S,6S)-3,4,5-triacetoxy-6-methyl-tetrahydro-thiopyran-2-yloxymethyl)-tetrahydro-pyran-4-yl ester 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以97%的产率得到5-thio-Fuc(a1-6)GlcNAc(b)-O-allyl
  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：

  2,3,4-tri-O-acetyl-5-thio-L-fucopyranosyl trichloroacetimidate 在 吡啶 、 三氟化硼乙醚 、 四丁基氟化铵 作用下， 反应 0.75h， 生成 Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-5-acetylamino-6-allyloxy-2-((2R,3S,4R,5S,6S)-3,4,5-triacetoxy-6-methyl-tetrahydro-thiopyran-2-yloxymethyl)-tetrahydro-pyran-4-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