β-D-arabinofuranosyl hexyl sulfone | 1159261-77-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: β-D-arabinofuranosyl hexyl sulfone
• 英文别名: (2S,3S,4S,5R)-2-hexylsulfonyl-5-(hydroxymethyl)oxolane-3,4-diol
• CAS: 1159261-77-4
• 化学式: C₁₁H₂₂O₆S
• 分子量: 282.358
• InChiKey: OPCMWJFWDPTEFB-ZNSHCXBVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  112
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2,3,5-tri-O-benzyl-β-D-arabinofuranosyl hexyl sulfone 在 palladium 10% on activated carbon 、 氢气 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 16.0h， 以82%的产率得到β-D-arabinofuranosyl hexyl 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

文献信息

• Stereoselective synthesis of β-arabino glycosyl sulfones as potential inhibitors of mycobacterial cell wall biosynthesis
  作者：Benjamin Ayers、Hilary Long、Edith Sim、Iain A. Smellie、Brendan L. Wilkinson、Antony J. Fairbanks

  DOI：10.1016/j.carres.2009.02.006

  日期：2009.4

  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.