1,3,4,6-tetra-O-acetyl-2-chloro-2-deoxy-D-glucopyranose | 873948-75-5

• 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-D-glucopyranose
• 英文别名: 1,3,4,6-tetra-O-acetyl-2-chloro-2-deoxy-α,β-D-glucopyranose；(3R,4S,5R,6R)-6-(Acetoxymethyl)-3-chlorotetrahydro-2H-pyran-2,4,5-triyl Triacetate；[(2R,3R,4S,5R)-3,4,6-triacetyloxy-5-chlorooxan-2-yl]methyl acetate
• CAS: 873948-75-5
• 化学式: C₁₄H₁₉ClO₉
• 分子量: 366.752
• InChiKey: XWFCBNNTEZQHTA-GNMOMJPPSA-N

物化性质

• 沸点：
  442.8±45.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

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

• 作为反应物：
  描述：

  1,3,4,6-tetra-O-acetyl-2-chloro-2-deoxy-D-glucopyranose 在 N-氯代丁二酰亚胺 、 碘苯二乙酸 、 氢溴酸 、 碘 、 乙酸酐 、 二乙胺 作用下， 以 四氢呋喃 、 氘代氯仿 、 二氯甲烷 、 水 、 溶剂黄146 为溶剂， 反应 4.5h， 生成 2,3,5-tri-O-acetyl-1,1,1-trichloro-1-deoxy-4-O-formyl-D-arabinitol
  参考文献：
  名称：

  Synthesis and stability of mixed nonfluorinated 1,1,1-trihalo-alkanes

  摘要：

  1, 1, 1-Trihaloalkanes of the types R-CCl2I, R-CClBrI, and R-CBr2I belonging to 1,1,1-trihalo-1-deoxy-D-arabinitol series of alditols were prepared and fully characterized by anomeric alkoxyl radical fragmentation of the corresponding 2,2-dihalo-2-deoxy-D-arabino-hexopyranose derivatives. The analogous diiodohalo compounds R-CClI2 and R-CBrI2 could not be prepared by this methodology. The results strongly suggest that the stability of the mixed trihalo alditols decreases with increasing bulkiness of the halogen atoms. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.10.118
• 作为产物：
  描述：

  乙酰化葡萄烯糖 在 4-二甲氨基吡啶 、 N-氯代丁二酰亚胺 作用下， 以 四氢呋喃 、 吡啶 、 水 为溶剂， 反应 16.0h， 生成 1,3,4,6-tetra-O-acetyl-2-chloro-2-deoxy-D-glucopyranose
  参考文献：
  名称：

  Synthesis and stability of mixed nonfluorinated 1,1,1-trihalo-alkanes

  摘要：

  1, 1, 1-Trihaloalkanes of the types R-CCl2I, R-CClBrI, and R-CBr2I belonging to 1,1,1-trihalo-1-deoxy-D-arabinitol series of alditols were prepared and fully characterized by anomeric alkoxyl radical fragmentation of the corresponding 2,2-dihalo-2-deoxy-D-arabino-hexopyranose derivatives. The analogous diiodohalo compounds R-CClI2 and R-CBrI2 could not be prepared by this methodology. The results strongly suggest that the stability of the mixed trihalo alditols decreases with increasing bulkiness of the halogen atoms. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.10.118

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.