1,3,4,6-tetra-O-acetyl-2-chloro-2-deoxy-β-D-glucopyranose | 25581-36-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,3,4,6-tetra-O-acetyl-2-chloro-2-deoxy-β-D-glucopyranose
• 英文别名: tetra-O-acetyl-2-chloro-2-deoxy-β-D-glucopyranose；Tetra-O-acetyl-2-chlor-2-desoxy-β-D-glucopyranose；[(2R,3R,4S,5R,6S)-3,4,6-triacetyloxy-5-chlorooxan-2-yl]methyl acetate
• CAS: 25581-36-6
• 化学式: C₁₄H₁₉ClO₉
• 分子量: 366.752
• InChiKey: XWFCBNNTEZQHTA-DHGKCCLASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.31
• 重原子数：
  24.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  114.43
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为产物：
  描述：

  乙酰化葡萄烯糖 在 四氯化碳 、 氯 、 溶剂黄146 作用下， 生成 1,3,4,6-tetra-O-acetyl-2-chloro-2-deoxy-β-D-glucopyranose
  参考文献：
  名称：

  Fischer,E.; Bergmann; Schotte, Chemische Berichte, 1920, vol. 53, p. 520

  摘要：

  DOI：

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.