2,3,4,6-tetra-O-(trideuteroacetyl)-α-D-glucopyranosyl bromide | 139639-90-0

• 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-(trideuteroacetyl)-α-D-glucopyranosyl bromide
• CAS: 139639-90-0
• 化学式: C₁₄H₁₉BrO₉
• 分子量: 423.108
• InChiKey: CYAYKKUWALRRPA-NSQVRNKBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.46
• 重原子数：
  24.0
• 可旋转键数：
  9.0
• 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：

  2,3,4,6-tetra-O-(trideuteroacetyl)-α-D-glucopyranosyl bromide 、 1,2,3,4-四-O-乙酰基-β-D-葡萄吡喃糖 在 氰化汞 作用下， 以 硝基甲烷 、 苯 为溶剂， 生成 (2S,3R,4S,5R,6R)-6-((((2R,3R,4S,5R,6R)-3,4,5-tris(acetoxy-d3)-6-((acetoxy-d3)methyl)tetrahydro-2H-pyran-2-yl)oxy)methyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate
  参考文献：
  名称：

  Study of selected ions in the ammonia desorption chemical ionization mass spectra of peracetylated gentiobiose and two isotopically labelled peracetylated gentiobioses

  摘要：

  AbstractThe ammonia desorption chemical ionization (NH3‐DCI) mass spectra of peracetylated gentiobiose (1) and two isotopically labelled gentiobioses (2 and 3) were examined. Compound 2 is labelled with trideuteroacetyl groups in the non‐reducing moiety and 3 with trideuteroacetyl groups in the reducing moiety. It is shown that the [M + NH4 – 42]+ ion is not formed direct from [M + NH4]+ by loss of ketene but appears to be formed by way of a nucleophilic acyl substitution reaction resulting in a neutral species which complexes with NH4+. The disaccharides undergo cleavage at either side of the glycosidic oxygen joining the two sugar residues, a process which is accompanied by addition of H or CH3CO to afford neutral species which complex with NH4+. The structures of the ions resulting from H transfer have been inferred by comparison of their mass‐analysed ion kinetic energy (MIKE) spectra with MIKE spectra of the [M + NH4]+ ions of compounds of established structure. A ring fragmentation reaction of 1, 2 and 3 is reported.

  DOI：

  10.1002/oms.1210270108