5-deoxy-5-[2,3,5-tri-O-benzyl-1,4-dideoxy-1,4-episulfoniumylidene-D-arabinitol]-1,2-O-isopropylidene-3-O-sulfoxy-α-D-xylofuranose inner salt | 878288-84-7

• 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: 5-deoxy-5-[2,3,5-tri-O-benzyl-1,4-dideoxy-1,4-episulfoniumylidene-D-arabinitol]-1,2-O-isopropylidene-3-O-sulfoxy-α-D-xylofuranose inner salt
• CAS: 878288-84-7
• 化学式: C₃₄H₄₀O₁₀S₂
• 分子量: 672.818
• InChiKey: WPKSHLBZYHBASK-ZZSFTUBRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  46.0
• 可旋转键数：
  14.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  121.81
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  5-deoxy-5-[2,3,5-tri-O-benzyl-1,4-dideoxy-1,4-episulfoniumylidene-D-arabinitol]-1,2-O-isopropylidene-3-O-sulfoxy-α-D-xylofuranose inner salt 在 palladium on activated charcoal 氢气 、 三氟乙酸 作用下， 以 甲醇 、 水 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 21.0h， 生成 3-O-sulfoxy-5-deoxy-5-[1,4-dideoxy-1,4-episulfoniumylidene-D-arabinitol]-α-D-xylofuranose inner salt
  参考文献：
  名称：

  Synthesis of Sulfonium Sulfate Analogues of Disaccharides and Their Conversion to Chain-Extended Homologues of Salacinol: New Glycosidase Inhibitors

  摘要：

  [graphics]Four chain extended homologues of salacinol, a naturally occurring glycosidase inhibitor, were prepared for evaluation as inhibitors of glucosidase enzymes involved in the breakdown of carbohydrates. The syntheses involved the reactions of 1,4-anhydro-2,3,5-tri-O-benzyl-4-thiO-D-arabinitol with cyclic sulfate derivatives of different monosaccharides. Debenzylation of the products afforded the novel sulfonium sulfate derivatives Of D-glucose, D-galactose, D-arabinose, and D-Xylose that are of interest in their own right as glycosidase inhibitors. Reduction to the corresponding alditols then afforded the homologues of salacinol containing polyhydroxylated, acyclic chains of 5- and 6-carbons, differing in stereochemistry at the stereogenic centers. Three of the chain-extended homologues inhibited recombinant human maltase glucoamylase, one of the key intestinal enzymes involved in the breakdown of glucose oligosaccharides in the sinall intestine, with K-i values in the low microinolar range, of approximately the saine inagnitude as salacinol, thus providing lead candidates for the treatment of Type 2 diabetes.

  DOI：

  10.1021/jo052252u
• 作为产物：
  描述：

  (2R,3S,4S)-3,4-双(苄氧基)-2-((苄氧基)甲基)四氢噻吩 、 1,2-O-isopropylidene-α-d-xylofuranose 3,5-cyclic sulfate 在 六氟异丙醇 作用下， 反应 44.0h， 以85%的产率得到5-deoxy-5-[2,3,5-tri-O-benzyl-1,4-dideoxy-1,4-episulfoniumylidene-D-arabinitol]-1,2-O-isopropylidene-3-O-sulfoxy-α-D-xylofuranose inner salt
  参考文献：
  名称：

  Synthesis of Sulfonium Sulfate Analogues of Disaccharides and Their Conversion to Chain-Extended Homologues of Salacinol: New Glycosidase Inhibitors

  摘要：

  [graphics]Four chain extended homologues of salacinol, a naturally occurring glycosidase inhibitor, were prepared for evaluation as inhibitors of glucosidase enzymes involved in the breakdown of carbohydrates. The syntheses involved the reactions of 1,4-anhydro-2,3,5-tri-O-benzyl-4-thiO-D-arabinitol with cyclic sulfate derivatives of different monosaccharides. Debenzylation of the products afforded the novel sulfonium sulfate derivatives Of D-glucose, D-galactose, D-arabinose, and D-Xylose that are of interest in their own right as glycosidase inhibitors. Reduction to the corresponding alditols then afforded the homologues of salacinol containing polyhydroxylated, acyclic chains of 5- and 6-carbons, differing in stereochemistry at the stereogenic centers. Three of the chain-extended homologues inhibited recombinant human maltase glucoamylase, one of the key intestinal enzymes involved in the breakdown of glucose oligosaccharides in the sinall intestine, with K-i values in the low microinolar range, of approximately the saine inagnitude as salacinol, thus providing lead candidates for the treatment of Type 2 diabetes.

  DOI：

  10.1021/jo052252u