2-bromo-2-deoxy-β-D-glucose | 141554-03-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-bromo-2-deoxy-β-D-glucose
• 英文别名: (2R,3R,4S,5S,6R)-3-bromo-6-(hydroxymethyl)oxane-2,4,5-triol
• CAS: 141554-03-2
• 化学式: C₆H₁₁BrO₅
• 分子量: 243.054
• InChiKey: PHZACKHLMJROHS-QZABAPFNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  90.2
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1,3,4,6-tetra-O-acetyl-2-bromo-2-deoxy-α,β-D-glucopyranose 在 盐酸 、 水 作用下， 生成 2-bromo-2-deoxy-β-D-glucose 、 2-deoxy-2-bromo-D-glucopyranose
  参考文献：
  名称：

  d-Glucose- and d-mannose-based antimetabolites. Part 2. Facile synthesis of 2-deoxy-2-halo-d-glucoses and -d-mannoses

  摘要：

  Modified D-glucose and D-mannose analogs are potentially clinically useful metabolic inhibitors. Biological evaluation of 2-deoxy-2-halo analogs has been impaired by limited availability and lack of efficient methods for their preparation. We have developed practical synthetic approaches to 2-deoxy-2-fluoro-, 2-chloro-2-deoxy-, 2-bromo-2-deoxy-, and 2-deoxy-2-iodo derivatives Of D-glucose and D-mannose that exploit electrophilic addition reactions to a commercially available 3,4,6-tri-O-acetyl-D-glucal. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2009.06.016

文献信息

• d-Glucose- and d-mannose-based antimetabolites. Part 2. Facile synthesis of 2-deoxy-2-halo-d-glucoses and -d-mannoses
  作者：Izabela Fokt、Slawomir Szymanski、Stanislaw Skora、Marcin Cybulski、Timothy Madden、Waldemar Priebe

  DOI：10.1016/j.carres.2009.06.016

  日期：2009.8

  Modified D-glucose and D-mannose analogs are potentially clinically useful metabolic inhibitors. Biological evaluation of 2-deoxy-2-halo analogs has been impaired by limited availability and lack of efficient methods for their preparation. We have developed practical synthetic approaches to 2-deoxy-2-fluoro-, 2-chloro-2-deoxy-, 2-bromo-2-deoxy-, and 2-deoxy-2-iodo derivatives Of D-glucose and D-mannose that exploit electrophilic addition reactions to a commercially available 3,4,6-tri-O-acetyl-D-glucal. (C) 2009 Elsevier Ltd. All rights reserved.