(1S,2R,3S,4S)-3,4-bis(benzyloxy)-1-(((2S,3S,4S,5R,6S)-6-(benzyloxy)-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)methyl)-2-((benzyloxy)methyl)tetrahydro-1H-thiophen-1-ium 4-methylbenzenesulfonate | 1220095-44-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,2R,3S,4S)-3,4-bis(benzyloxy)-1-(((2S,3S,4S,5R,6S)-6-(benzyloxy)-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)methyl)-2-((benzyloxy)methyl)tetrahydro-1H-thiophen-1-ium 4-methylbenzenesulfonate
• CAS: 1220095-44-2
• 化学式: C₇H₇O₃S*C₃₉H₄₅O₈S
• 分子量: 845.044
• InChiKey: KMBWMWSDMUDLTC-YSYOHUIQSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  59.0
• 可旋转键数：
  16.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  164.04
• 氢给体数：
  3.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  (1S,2R,3S,4S)-3,4-bis(benzyloxy)-1-(((2S,3S,4S,5R,6S)-6-(benzyloxy)-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)methyl)-2-((benzyloxy)methyl)tetrahydro-1H-thiophen-1-ium 4-methylbenzenesulfonate 在 三氯化硼 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 9.5h， 生成
  参考文献：
  名称：

  Potent Glucosidase Inhibitors: De-O-sulfonated Ponkoranol and Its Stereoisomer

  摘要：

  Ponkoranol, a glucosidase inhibitor isolated from the plant Salacia reticulata, comprises a sulfonium ion with an internal sulfate counterion. An efficient synthetic route to de-O-sulfonated ponkoranol and its 5'-stereoisomer is reported, and it is shown that these compounds are potent glucosidase inhibitors that inhibit a key intestinal human glucosidase, the N-terminal catalytic domain of maltase glucoamylase, with K, values of 43 +/- 3 and 15 +/- 1 nM, respectively.

  DOI：

  10.1021/ol1004005
• 作为产物：
  描述：

  benzyl 6-O-p-toluene-sulfonyl-α-D-glucopyranoside 、 (2R,3S,4S)-3,4-双(苄氧基)-2-((苄氧基)甲基)四氢噻吩 在 potassium carbonate 作用下， 以 六氟异丙醇 为溶剂， 反应 96.0h， 以52%的产率得到(1S,2R,3S,4S)-3,4-bis(benzyloxy)-1-(((2S,3S,4S,5R,6S)-6-(benzyloxy)-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)methyl)-2-((benzyloxy)methyl)tetrahydro-1H-thiophen-1-ium 4-methylbenzenesulfonate
  参考文献：
  名称：

  Potent Glucosidase Inhibitors: De-O-sulfonated Ponkoranol and Its Stereoisomer

  摘要：

  Ponkoranol, a glucosidase inhibitor isolated from the plant Salacia reticulata, comprises a sulfonium ion with an internal sulfate counterion. An efficient synthetic route to de-O-sulfonated ponkoranol and its 5'-stereoisomer is reported, and it is shown that these compounds are potent glucosidase inhibitors that inhibit a key intestinal human glucosidase, the N-terminal catalytic domain of maltase glucoamylase, with K, values of 43 +/- 3 and 15 +/- 1 nM, respectively.

  DOI：

  10.1021/ol1004005