2,3,4,6-tetra-O-methyl-α-D-mannopyranosyl bromide | 95042-46-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4,6-tetra-O-methyl-α-D-mannopyranosyl bromide
• 英文别名: (2R,3S,4S,5R,6R)-2-bromo-3,4,5-trimethoxy-6-(methoxymethyl)oxane
• CAS: 95042-46-9
• 化学式: C₁₀H₁₉BrO₅
• 分子量: 299.162
• InChiKey: DFXATGFXDBFSEZ-ZJDVBMNYSA-N

物化性质

• 沸点：
  318.9±42.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetra-O-methyl-α-D-mannopyranosyl bromide 、 钾[锰(五羰基)] 以 乙醚 为溶剂， 以28%的产率得到2,3,4,6-tetra-O-methyl-β-D-mannopyranosylmanganese pentacarbonyl
  参考文献：
  名称：

  Glycosylmanganese pentacarbonyl complexes: an organomanganese-based approach to the synthesis of C-glycosyl derivatives

  摘要：

  Preparation, structure and reactions of glycosylmanganese pentacarbonyl complexes are discussed. Anomerically pure complexes of pyranosyl and furanosyl complexes were prepared in excellent yield. The conformations of the anomeric glucosyl and mannosyl complexes were derived from detailed analysis of their 1D and 2D H-1- and C-13-NMR spectra including NOE data. The complexes are further characterized by Mn-55-NMR chemical shifts and Mn-55, C-13 one-bond coupling constants. These compounds undergo various migratory insertion reactions resulting in formation of C-glycosyl derivatives. Applications of this technology to the synthesis of C-glycosyl and C-aryl glycosidic systems are discussed. (C) 2000 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0022-328x(99)00431-3
• 作为产物：
  描述：

  phenyl 2,3,4,6-tetra-O-methyl-1-deoxy-1-thio-α-D-mannopyranoside 在 溴 作用下， 以 二氯甲烷 为溶剂， 以74%的产率得到2,3,4,6-tetra-O-methyl-α-D-mannopyranosyl bromide
  参考文献：
  名称：

  Are Glycosyl Triflates Intermediates in the Sulfoxide Glycosylation Method? A Chemical and ¹H, ¹³C, and ¹⁹F NMR Spectroscopic Investigation

  摘要：

  The title question is addressed by low-temperature H-1, C-13, and F-19 NMR spectroscopies in CD2Cl2 as well as by the preparation of authentic samples from glycopyranosyl bromides and AgOTf. At -78 degrees C glycosyl triflates are cleanly generated with either nonparticipating or particpating protecting groups at O-2. The glycosyl triflates identified in this manner were allowed to react with methanol, resulting in the formation of methyl glycosides. Glycosyl triflates were generated at -78 degrees C in CD2Cl2 and allowed to warm gradually until decomposition was detected by H-1 and F-19 NMR spectroscopy. The decomposition temperature and products are functions of the protecting groups employed.

  DOI：

  10.1021/ja971239r