1,2,3,4-Tetra-O-acetyl-6-bromo-6-deoxy-α-D-glucopyranose | 7404-34-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1,2,3,4-Tetra-O-acetyl-6-bromo-6-deoxy-α-D-glucopyranose
• 英文别名: 1,2,3,4-tetra-O-acetyl-6-deoxy-6-bromo-α-D-glucopyranose；tetra-O-acetyl-6-bromo-6-deoxy-α-D-glucopyranose；Tetra-O-acetyl-6-brom-6-desoxy-α-D-glucopyranose；α-Tetraacetyl-6-brom-6-desoxy-D-glucose；alpha-D-Glucopyranose, 6-bromo-6-deoxy-, tetraacetate；[(2S,3S,4S,5R,6R)-4,5,6-triacetyloxy-2-(bromomethyl)oxan-3-yl] acetate
• CAS: 7404-34-4；10225-48-6；29884-71-7；50618-17-2
• 化学式: C₁₄H₁₉BrO₉
• 分子量: 411.203
• InChiKey: VJAPWODGPODCIG-RGDJUOJXSA-N

物化性质

• 熔点：
  170-170.5 °C
• 沸点：
  425.4±45.0 °C(Predicted)
• 密度：
  1.49±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  114
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1,2,3,4-Tetra-O-acetyl-6-bromo-6-deoxy-α-D-glucopyranose 在 丙酮 、 sodium iodide 作用下， 生成 acetoxy α-D-2,3,4-triacetoxy-6-deoxy-6-iodoglucopyranoside
  参考文献：
  名称：

  Helferich; Himmen, Chemische Berichte, 1928, vol. 61, p. 1825,1833

  摘要：

  DOI：
• 作为产物：
  描述：

  6-bromo-6-deoxy-D-glucopyranose 、 乙酸酐 在 吡啶 作用下， 生成 1,2,3,4-Tetra-O-acetyl-6-bromo-6-deoxy-α-D-glucopyranose
  参考文献：
  名称：

  在未保护的碳水化合物或糖苷中伯醇的区域选择性溴化的新协议。

  摘要：

  在干燥的DMF中，在四丁基溴化铵（TBAB）存在下，使用（氯-苯硫基-亚甲基）二甲基氯化铵（CPMA）成功地实现了未保护的碳水化合物或糖苷中伯羟基的区域选择性和有效溴化。

  DOI：

  10.1002/cjoc.201200211

文献信息

• Freudenberg et al., Chemische Berichte, 1928, vol. 61, p. 1735,1738
  作者：Freudenberg et al.

  DOI：——

  日期：——
• Micheel, Chemische Berichte, 1957, vol. 90, p. 1612,1615
  作者：Micheel

  DOI：——

  日期：——
• Ohle; Marecek, Chemische Berichte, 1930, vol. 63, p. 612,627
  作者：Ohle、Marecek

  DOI：——

  日期：——
• Wrede, Hoppe-Seyler's Zeitschrift fur Physiologische Chemie, 1921, vol. 115, p. 284,290
  作者：Wrede

  DOI：——

  日期：——
• The search for d-glucose derivatives suitable for the study of natural hydrogen isotope fractionation
  作者：J.Michael Williams、Hélène Jegou、Virginie Langlois、Ben-Li Zhang、Maryvonne L. Martin

  DOI：10.1016/0008-6215(93)80059-n

  日期：1993.7

  In order to apply Site-specific Natural Isotope Fractionation (SNIF) to chemical, biochemical, and environmental studies Of D-glucose, there is a need for readily prepared compounds which give H-2 NMR spectra with all or most signals resolved. Changing substituents at C-1 and/or C-6 of alpha-D-glucopyranose pentaacetate improved the dispersion of deuterium signals, the best results being achieved with 1,2,3,4-tetra-O-acetyl-6-deoxy-6-thiocyanato-alpha-D-glucopyranose, for which only the H-2-2 and 2 H-4 signals were not resolved, and with 2,3,4-tri-O-acetyl-6-bromo-6-deoxy-alpha-D-glucopyranosyl bromide, for which only the H-2-6a and H-2-6b signals were not resolved. Periodate oxidation of methyl 4,6-O-benzylidene-alpha-D-glucopyranoside and 4,6-dichloro-4,6-dideoxy-D-galactose was also examined as a possible source of useful compounds. Products obtained from the benzylideneglucoside gave inadequate resolution and broad deuterium signals. The oxidation of 4,6-dichloro-4,6-dideoxy-D-galactose was not straightforward. The a anomer was oxidised more rapidly than the beta anomer. The oxidation product, 2,4-dichloro-2,4-dideoxy-3-O-formyl-D-threose, was too labile to be isolated pure and its hydrolysis to 2,4-dichloro-2,4-dideoxy-D-threose was accompanied by a slow elimination to form 2,4-dichlorobut-2-enal.