2-benzylsulfanyl-4,5-dihydro-3-O-tert-butyldimethylsilyl-1,2,5-trideoxy-5-iodo-β-D-arabinofuranoso-[2,1-d]-1,3-oxazole | 1562996-02-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-benzylsulfanyl-4,5-dihydro-3-O-tert-butyldimethylsilyl-1,2,5-trideoxy-5-iodo-β-D-arabinofuranoso-[2,1-d]-1,3-oxazole
• CAS: 1562996-02-4
• 化学式: C₁₉H₂₈INO₃SSi
• 分子量: 505.492
• InChiKey: NDNHVPOZLYZXLL-WCXIOVBPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.22
• 重原子数：
  26.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  40.05
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2-benzylsulfanyl-4,5-dihydro-3-O-tert-butyldimethylsilyl-1,2,5-trideoxy-5-iodo-β-D-arabinofuranoso-[2,1-d]-1,3-oxazole 在 溶剂黄146 、 锌 作用下， 反应 1.0h， 以86%的产率得到2-benzylsulfanyl-5-[(1R)-1-tert-butyldimethylsilyloxyprop-2-en-1-yl]-4,5-dihydro-4-hydroxy-1,3-oxazole
  参考文献：
  名称：

  Synthesis and Antimicrobial Evaluation of Oxazole-2(3H)-thione and 2-Alkylsulfanyl-1,3-oxazole Derivatives

  摘要：

  The preparation of oxazole-2(3B)-thiones (OXTs) by condensation of thiocyanic acid on a-hydroxycarbonyl substrates has been revisited. Extension to more complex scaffolds afforded chiral OXTs, whereas carbohydrate-fused 2-alkylsulfanyl-1,3-oxazolines led to original hemiaminal structures. A survey of the reactivity of OXTs with various electrophiles showed S- or N-chemoselectivity based on HSAB parameters. Antimicrobial evaluation of selected synthesized compounds was carried out, from which the hemiaminal 15 emerged as a promising antifungal agent.

  DOI：

  10.3987/com-13-s(s)56
• 作为产物：
  描述：

  (1,2,5-trideoxy-5-iodo-β-D-arabinofuranoso)[2,1-d]oxazolidine-2-thione 在 咪唑 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 2-benzylsulfanyl-4,5-dihydro-3-O-tert-butyldimethylsilyl-1,2,5-trideoxy-5-iodo-β-D-arabinofuranoso-[2,1-d]-1,3-oxazole
  参考文献：
  名称：

  Synthesis and Antimicrobial Evaluation of Oxazole-2(3H)-thione and 2-Alkylsulfanyl-1,3-oxazole Derivatives

  摘要：

  The preparation of oxazole-2(3B)-thiones (OXTs) by condensation of thiocyanic acid on a-hydroxycarbonyl substrates has been revisited. Extension to more complex scaffolds afforded chiral OXTs, whereas carbohydrate-fused 2-alkylsulfanyl-1,3-oxazolines led to original hemiaminal structures. A survey of the reactivity of OXTs with various electrophiles showed S- or N-chemoselectivity based on HSAB parameters. Antimicrobial evaluation of selected synthesized compounds was carried out, from which the hemiaminal 15 emerged as a promising antifungal agent.

  DOI：

  10.3987/com-13-s(s)56