benzyl 3-O-benzyl-2,4-bis(dibenzylphosphoryl)-6-O-ethylsulfonyl-D-glucopyranoside | 1216905-14-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 3-O-benzyl-2,4-bis(dibenzylphosphoryl)-6-O-ethylsulfonyl-D-glucopyranoside
• CAS: 1216905-14-4
• 化学式: C₅₀H₅₄O₁₄P₂S
• 分子量: 972.984
• InChiKey: PCNFBOVBWWKKAB-ULJHBXBISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.73
• 重原子数：
  67.0
• 可旋转键数：
  26.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  160.58
• 氢给体数：
  0.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  benzyl 3-O-benzyl-2,4-bis(dibenzylphosphoryl)-6-O-ethylsulfonyl-D-glucopyranoside 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 、 水 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 16.0h， 以89%的产率得到6-O-ethylsulfonyl-D-glucose 2,4-diphosphate
  参考文献：
  名称：

  Development of carbohydrate-derived inhibitors of acid sphingomyelinase

  摘要：

  The acid sphingomyelinase is an emerging drug target, especially for inflammatory lung diseases. Presently, there are no directly-acting potent inhibitors available for cell-based studies. The potent inhibitor phosphatidylinositol-3,5-bisphosphate (PtdIns3,5P2) is not only unsuited for cell culture studies, but also does not provide hints for further structural improvements. In the SAR study described here, we replaced the inositolphosphate moiety by a carbohydrate derivative and the phosphatidic acid residue by an alkyl-sulfone ester. The resulting compound is more active than its parent compound and offers new means for further structural modification. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.11.030
• 作为产物：
  描述：

  benzyl 3-O-benzyl-6-O-ethylsulfonyl-D-glucopyranoside 、 二苯基N,N'-二异丙基亚磷酰胺 在 四氮唑 、 叔丁基过氧化氢 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以54%的产率得到benzyl 3-O-benzyl-2,4-bis(dibenzylphosphoryl)-6-O-ethylsulfonyl-D-glucopyranoside
  参考文献：
  名称：

  Development of carbohydrate-derived inhibitors of acid sphingomyelinase

  摘要：

  The acid sphingomyelinase is an emerging drug target, especially for inflammatory lung diseases. Presently, there are no directly-acting potent inhibitors available for cell-based studies. The potent inhibitor phosphatidylinositol-3,5-bisphosphate (PtdIns3,5P2) is not only unsuited for cell culture studies, but also does not provide hints for further structural improvements. In the SAR study described here, we replaced the inositolphosphate moiety by a carbohydrate derivative and the phosphatidic acid residue by an alkyl-sulfone ester. The resulting compound is more active than its parent compound and offers new means for further structural modification. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.11.030