decyl 2,3,5-tri-O-benzyl-1-thio-β-D-arabinofuranoside | 1159261-65-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: decyl 2,3,5-tri-O-benzyl-1-thio-β-D-arabinofuranoside
• CAS: 1159261-65-0
• 化学式: C₃₆H₄₈O₄S
• 分子量: 576.841
• InChiKey: LAFLAGBRQJTURU-NWJWHWDBSA-N

物化性质

• 沸点：
  669.4±55.0 °C(predicted)
• 密度：
  1.10±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.97
• 重原子数：
  41.0
• 可旋转键数：
  20.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  36.92
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  decyl 2,3,5-tri-O-benzyl-1-thio-β-D-arabinofuranoside 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以88%的产率得到2,3,5-tri-O-benzyl-β-D-arabinofuranosyl decyl sulfone
  参考文献：
  名称：

  Stereoselective synthesis of β-arabino glycosyl sulfones as potential inhibitors of mycobacterial cell wall biosynthesis

  摘要：

  A series of beta-arabino glycosyl sulfones with varying alkyl chain lengths were synthesised in a stereoselective fashion as putative mimics of decaprenolphosphoarabinose (DPA), and as potential inhibitors of mycobacterial cell wall biosynthesis. Biological testing against Mycobacterium bovis BCG revealed low to moderate anti-mycobacterial activity with marked dependence on alkyl chain length, which was maximal for a C-12 chain. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2009.02.006
• 作为产物：
  描述：

  2,3,5-tri-O-benzyl-D-arabinofuranosyl bromide 、 1-癸硫醇 在 2,4,6-三叔丁基嘧啶 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以80%的产率得到decyl 2,3,5-tri-O-benzyl-1-thio-β-D-arabinofuranoside
  参考文献：
  名称：

  Stereoselective synthesis of β-arabino glycosyl sulfones as potential inhibitors of mycobacterial cell wall biosynthesis

  摘要：

  A series of beta-arabino glycosyl sulfones with varying alkyl chain lengths were synthesised in a stereoselective fashion as putative mimics of decaprenolphosphoarabinose (DPA), and as potential inhibitors of mycobacterial cell wall biosynthesis. Biological testing against Mycobacterium bovis BCG revealed low to moderate anti-mycobacterial activity with marked dependence on alkyl chain length, which was maximal for a C-12 chain. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2009.02.006