1,4-anhydro-2-deoxy-2-fluoro-3,5-di-O-(p-methoxybenzyl)-4-thio-D-arabinitol | 1023292-14-9

• 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: 1,4-anhydro-2-deoxy-2-fluoro-3,5-di-O-(p-methoxybenzyl)-4-thio-D-arabinitol
• 英文别名: (2R,3S,4S)-4-fluoro-3-[(4-methoxyphenyl)methoxy]-2-[(4-methoxyphenyl)methoxymethyl]thiolane
• CAS: 1023292-14-9
• 化学式: C₂₁H₂₅FO₄S
• 分子量: 392.492
• InChiKey: SIUJRLOHIVEGDV-NJYVYQBISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  62.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,4-anhydro-2-deoxy-2-fluoro-3,5-di-O-(p-methoxybenzyl)-4-thio-D-arabinitol 、 2,4-O-benzylidene-L-erythritol-1,3-cyclic sulfate 在 potassium carbonate 作用下， 以 various solvent(s) 为溶剂， 以70%的产率得到1,2,4-trideoxy-2-fluoro-3,5-di-O-p-methoxybenzyl-1,4-[[(2S,3S)-2,4-O-benzylidene-3-(sulfooxy)butyl]episulfoniumylidene]-D-arabinitol inner salt
  参考文献：
  名称：

  Synthesis of 2-deoxy-2-fluoro and 1,2-ene derivatives of the naturally occurring glycosidase inhibitor, salacinol, and their inhibitory activities against recombinant human maltase glucoamylase

  摘要：

  2-Deoxy-2-fluorosalacinol and a 1,2-ene derivative of the naturally occurring glycosidase inhibitor salacinol were synthesized for structure activity studies with human maltase glucoamylase (MGA). 2-Deoxy-2-fluorosalacinol was synthesized through the coupling reaction of 2-deoxy-2-fluoro-3,5-di-O-p-methoxybenzyl-1,4-anhydro-4-thio-D-arabinitol with 2,4-O-benzylidene-L-crythritol-1,3-cyclic sulfate in hexafluoroisopropanol (HFIP) containing 0.3 equiv of K2CO3. Excess of K2CO3 resulted in the elimination of HF from the coupled product, and the formation of an alkene derivative of salacinol. Nucleophilic attack of the 1,4-anhydro-4-thio-D-arabinitol moiety on the cyclic sulfate did not proceed in the absence of K2CO3. No reaction was observed in acetonitrile containing K2CO3. The target compounds were obtained by deprotection with TFA. The 2-deoxy-1-ene derivative of salacinol and 2-deoxy-2-fluorosalacinol inhibited recombinant human maltase glucoamylase, one of the key intestinal enzymes involved in the breakdown of glucose, with an IC50 value of 150 mu M and a K-i value of 6 +/- 1 mu M, respectively. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.01.025
• 作为产物：
  描述：

  1,4-anhydro-2-deoxy-2-fluoro-4-thio-D-arabinitol 、 4-甲氧基氯苄 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以1.1 g的产率得到1,4-anhydro-2-deoxy-2-fluoro-3,5-di-O-(p-methoxybenzyl)-4-thio-D-arabinitol
  参考文献：
  名称：

  Synthesis of 2-deoxy-2-fluoro and 1,2-ene derivatives of the naturally occurring glycosidase inhibitor, salacinol, and their inhibitory activities against recombinant human maltase glucoamylase

  摘要：

  2-Deoxy-2-fluorosalacinol and a 1,2-ene derivative of the naturally occurring glycosidase inhibitor salacinol were synthesized for structure activity studies with human maltase glucoamylase (MGA). 2-Deoxy-2-fluorosalacinol was synthesized through the coupling reaction of 2-deoxy-2-fluoro-3,5-di-O-p-methoxybenzyl-1,4-anhydro-4-thio-D-arabinitol with 2,4-O-benzylidene-L-crythritol-1,3-cyclic sulfate in hexafluoroisopropanol (HFIP) containing 0.3 equiv of K2CO3. Excess of K2CO3 resulted in the elimination of HF from the coupled product, and the formation of an alkene derivative of salacinol. Nucleophilic attack of the 1,4-anhydro-4-thio-D-arabinitol moiety on the cyclic sulfate did not proceed in the absence of K2CO3. No reaction was observed in acetonitrile containing K2CO3. The target compounds were obtained by deprotection with TFA. The 2-deoxy-1-ene derivative of salacinol and 2-deoxy-2-fluorosalacinol inhibited recombinant human maltase glucoamylase, one of the key intestinal enzymes involved in the breakdown of glucose, with an IC50 value of 150 mu M and a K-i value of 6 +/- 1 mu M, respectively. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.01.025