benzyl 2-O-benzyl-α-D-arabinofuranoside | 878288-79-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 2-O-benzyl-α-D-arabinofuranoside
• 英文别名: (2R,3R,4S,5S)-2-(hydroxymethyl)-4,5-bis(phenylmethoxy)oxolan-3-ol
• CAS: 878288-79-0
• 化学式: C₁₉H₂₂O₅
• 分子量: 330.381
• InChiKey: KFTDNYVPCVUJDL-YRXWBPOGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  68.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  benzyl 2-O-benzyl-α-D-arabinofuranoside 在 ruthenium trichloride 、 sodium periodate 、 氯化亚砜 、 三乙胺 作用下， 以 四氯化碳 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 0.75h， 生成 benzyl 2-O-benzyl-α-D-arabinofuranoside-3,5-cyclic sulfide
  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：

  benzyl 2,3,5-tri-O-benzoyl-α-D-arabinofuranoside 在 吡啶 、 四丁基氟化铵 、 sodium methylate 、 sodium iodide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 benzyl 2-O-benzyl-α-D-arabinofuranoside
  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

文献信息

• US8389565B2
  申请人：——

  公开号：US8389565B2

  公开（公告）日：2013-03-05
• Synthesis of Sulfonium Sulfate Analogues of Disaccharides and Their Conversion to Chain-Extended Homologues of Salacinol: New Glycosidase Inhibitors
  作者：Blair D. Johnston、Henrik H. Jensen、B. Mario Pinto

  DOI：10.1021/jo052252u

  日期：2006.2.1

  [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.